EP2168957B1 - Alkyl-substituted tetrahydropyranes as aromatic materials - Google Patents
Alkyl-substituted tetrahydropyranes as aromatic materials Download PDFInfo
- Publication number
- EP2168957B1 EP2168957B1 EP09176696A EP09176696A EP2168957B1 EP 2168957 B1 EP2168957 B1 EP 2168957B1 EP 09176696 A EP09176696 A EP 09176696A EP 09176696 A EP09176696 A EP 09176696A EP 2168957 B1 EP2168957 B1 EP 2168957B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- menthyl
- tetrahydropyran
- atoms
- branched
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000463 material Substances 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 title description 2
- 125000001412 tetrahydropyranyl group Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 109
- 239000000126 substance Substances 0.000 claims abstract description 55
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- 230000000694 effects Effects 0.000 claims abstract description 36
- 238000002360 preparation method Methods 0.000 claims abstract description 34
- 238000001816 cooling Methods 0.000 claims abstract description 33
- 150000003527 tetrahydropyrans Chemical class 0.000 claims abstract description 33
- 239000002324 mouth wash Substances 0.000 claims abstract description 19
- 229940051866 mouthwash Drugs 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
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- PEQQJYRAGJVBGC-UHFFFAOYSA-N 2-methyl-3-propyloxane Chemical compound CCCC1CCCOC1C PEQQJYRAGJVBGC-UHFFFAOYSA-N 0.000 claims abstract description 4
- XNSLICFTTNVZMG-UHFFFAOYSA-N 3-butyl-2-methyloxane Chemical compound CCCCC1CCCOC1C XNSLICFTTNVZMG-UHFFFAOYSA-N 0.000 claims abstract description 4
- REJQPVBZMKPAAI-UHFFFAOYSA-N 6-methyl-2-(2-methylpropyl)-3-prop-1-en-2-yloxane Chemical compound CC(C)CC1OC(C)CCC1C(C)=C REJQPVBZMKPAAI-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
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- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- PSBALWGXLHHTHS-UHFFFAOYSA-N 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran Chemical compound CCC1OC(C)(CC)CCC1C(C)C PSBALWGXLHHTHS-UHFFFAOYSA-N 0.000 claims description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
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- VUNOFAIHSALQQH-UHFFFAOYSA-N Ethyl menthane carboxamide Chemical compound CCNC(=O)C1CC(C)CCC1C(C)C VUNOFAIHSALQQH-UHFFFAOYSA-N 0.000 claims description 4
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- 239000011718 vitamin C Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000001243 zingiber officinale rosc. root absolute Substances 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/385—Concentrates of non-alcoholic beverages
- A23L2/39—Dry compositions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/24—Thermal properties
- A61K2800/244—Endothermic; Cooling; Cooling sensation
Definitions
- the present invention relates to alkyl-substituted tetrahydropyrans of the following formula (I), mixtures comprising these alkyl-substituted tetrahydropyrans, their respective use and corresponding aromatized products.
- the invention relates to the use of these flavorings in aroma and flavor compositions having a fresh effect for use in oral hygiene products.
- the invention further relates to preparations and rhinologica which cause a fresh and liberating sensation in the area of the mouth, throat and respiratory tract and preparations containing these compounds.
- Flavoring or flavoring compositions with freshness effect impart e.g. Oral hygiene products, such as toothpastes and mouthwashes, and sweets such as sweets and chewing gum, their typical, fresh and pleasant taste.
- Substances that are widely used for the preparation of such fresh flavoring or flavoring compositions include eucalyptol (1,8-cineole) and menthol.
- the use of these substances has some disadvantages.
- Eucalyptol has a very strong medicinal taste, which many consumers find repulsive, especially when Eucalyptol is used in higher doses.
- menthol With the use of menthol, the freshness effect begins with a certain delay, and at higher dosages the menthol develops a bitter-sharp taste, which has a rather unpleasant effect.
- the primary object of the present invention to provide compounds or mixtures of compounds which result in flavor and / or flavor compositions with freshness effect to an intensified, quickly perceptible freshness experience.
- the compounds or mixtures of compounds to be indicated should preferably have the lowest possible intrinsic taste, especially little or no medicinal and / or bitter taste.
- novel tetrahydropyrans according to the invention exhibit an effect related to the 1,8-cineol (eucalyptol) with respect to a fresh liberating sensation in the mouth, pharynx and respiratory tract, without producing an unpleasant taste sensation.
- the tetrahydropyrans according to the invention are distinguished essentially by a neutral, fresh-cool taste. They are therefore ideal for use in flavor and flavor compositions. Noteworthy is their ability to increase in aroma and flavor compositions, the intensity and the power of freshness feeling.
- an alkylated tetrahydropyran of the formula (I) is indicated: in which each R1 independently either hydrogen or a branched or unbranched alkyl radical having 1 to 3 C atoms or a branched or unbranched alkenyl radical having 2 to 3 C atoms, and R 2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms and R 3 is a branched or unbranched alkyl radical having 1 to 5 C atoms, except 2,6-Dimethyl-3- (1-methylethenyl) tetrahydropyran (CA5 No.
- Alkylated tetrahydropyran derivatives are, for example, as sensorically active substances in, for example, US Pat Perfumer & Flavorist, Vol 17, 1992, 77-92 and in PAFAI Journal (1984), 6 (3), 15-18 described.
- aroma-intensifying properties have the in WO 02/41861 A1 described acyclic ethers.
- their effect does not set in immediately, but with a certain time lag.
- the advantage of all cyclic ethers according to the invention lies in the immediacy of their action ("boost effect").
- alkylated tetrahydropyrans are preferred. It is particularly preferred if the compound or one of the compounds is selected from those alkylated tetrahydropyrans of the formula (I) in which each R1 is independently a methyl, ethyl or vinyl radical, R 2 is isopropyl, isopropenyl, sec-butyl or sec-butenyl, and R3 is an unbranched alkyl radical having 1 to 3 carbon atoms.
- the compound or at least one of the compounds of the mixture is preferably such an alkylated tetrahydropyran in which each R1 is independently a methyl or ethyl radical, R2 is an isopropyl or sec-butyl radical, and R3 is a methyl or ethyl radical.
- the compound or one of the compounds of the mixture is selected from the group consisting of 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran, 2.6 Dimethyl 5-isopropyl-2-ethyltetrahydropyran, 2,6-dimethyl-5-isopropenyl-2-vinyltetrahydropyran, 2,6-diethyl-5-sec-butyl-2-methyltetrahydropyran, and 2,6-dimethyl-5- sec-butyl-2-ethyltetrahydropyran.
- a most preferred compound for achieving the object of the invention is 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran; correspondingly preferred are also mixtures according to the invention containing at least this compound.
- the invention is based on the surprising finding that alkylated tetrahydropyrans according to the invention quickly increase the fresh effect of aroma compositions (compositions containing one or more flavorings and / or flavorings) with a fresh effect without, however, having a strong intrinsic taste.
- the mixtures according to the invention consist of two, three, four or more compounds of the formula (I), preferably in each case in one of the embodiments given above as being preferred. It is furthermore preferred if, in a mixture to be used according to the invention, not only one compound of the formula (I) described above as being particularly preferred is present, d. H. not only a compound which comprises one, several or exclusively particularly preferred groups R 1, R 2 and R 3, but two or more particularly preferred compounds of the formula (I) according to the invention. Preferably, therefore, two, three or all compounds in a mixture according to the invention consisting of compounds of the formula (I) are selected from the group of compounds designated as preferred.
- the compounds of the formula (I) can be obtained according to the preparation methods known to the person skilled in the art.
- the compounds of formula (I) can be prepared in a process as illustrated in the scheme below.
- the reaction of the aldehyde (B) with the alcohol component (A) leads to the corresponding cyclized tetrahydropyran compound (C), which is to be subsumed under formula (I).
- Tetrahydropyran compound (C) may optionally be reduced in a second reaction step to the tetrahydropyran compound (D) which is also to be subsumed under formula (I).
- R1 and R3 each have the above-mentioned (optionally preferred) meaning
- R a , R b and R c independently of one another represent hydrogen, methyl or ethyl, with the proviso that R a , R b and R c in total contain 1 or 2 C atoms, ie that the radicals R a , R b and R c together with the two with #-labeled CH radicals total of the radical R 2 in formula (I).
- the reaction of alcohol (A) with aldehyde (B) is preferably carried out in the presence of acidic catalysts.
- acid catalysts e.g. inorganic acids such as phosphoric acid, polyphosphoric acid, hydrochloric acid, nitric acid, sulfuric acid, organic acids such as methanesulfonic acid, toluenesulfonic acid or trifluoroacetic acid can be used.
- solid acids such as acidic ion exchangers, acidic aluminosilicates or acidic zeolites can also be used.
- Further preferred acidic catalysts are Lewis acids such as AlX 3 , ZnX 2 , FeX 3 , TiX 4 , wherein X is a halide from the group chlorine, bromine or iodine, and BF 3 , in particular AlCl 3 , ZnCl 2 , FeCl 3 , TiCl 4 and BF 3 adducts.
- catalysts are sulfuric acid, phosphoric acid and BF 3 adducts, in particular BF 3 etherate.
- the molar ratio of alcohol (A) to aldehyde (B) is preferably in the range from 1: 5 to 1: 3, particularly preferably in the range from 1: 3 to 1: 1. Particularly preferred is a molar ratio of alcohol (A) to aldehyde (B) of 1 to 1.05-1.2 (ie, slight excess of aldehyde).
- the reaction temperature is preferably in the range of -20 ° C to 50 ° C, preferably in the range of -10 ° C to 40 ° C, and more preferably in the range of 0 ° C to 15 ° C.
- the reaction of (A) with (B) the following temperature profile is particularly preferred: first, the reaction of the alcohol component (A) with the aldehyde component (B) takes place in the cold (preferably at 0-10 ° C.). In the case of catalysis with a protic acid, the reaction mixture is then preferably subsequently heated to about 60-80 ° C. in order to achieve as complete a conversion as possible. However, such subsequent heating may be omitted in catalysis with a Lewis acid.
- Suitable hydrogenation catalysts for reducing the C-C double bond (s) present in compounds of the formula (C) are, for example, elements of the 8th subgroup of the Periodic Table. Particularly advantageous here are the elements nickel, palladium, platinum, rhodium, iridium, ruthenium and mixtures thereof, compounds and alloys. These catalysts can be applied, preferably in elemental and finely divided form, to carriers or together with other metals or their compounds.
- Preferred support materials include activated carbon, aluminum oxides, metal oxides, silica gels, zeolites, clays, clay granules, amorphous aluminum silicates, or other inorganic or polymeric supports.
- the hydrogen pressure in the hydrogenation reaction is in the range of 1 to 200 bar, preferably in the range of 1 to 100 bar, particularly preferably in the range of 5 to 50 bar.
- Compounds of formula (I) may be prepared by conventional methods, e.g. by distillation.
- the tetrahydropyrans according to the invention can be administered in pure form, combined with each other or in a particularly preferred form with flavoring and / or flavoring agents.
- flavoring agent s
- Cechlor Directive 88/388 / EEC 22 June 1988, published in OJ. L 184 of 15 July 1988, p. 61. Flavorings are according to this guideline:
- flavorings to be used according to the invention are listed in Sections 1 to 3 of the Commission Decision of 23 February 1999 on a list Flavorings used in or on foodstuffs prepared in accordance with Regulation (EC) No 2232/96 of the European Parliament and of the Council of 28 October 1996 (1999/217 / EC), to be published in the Official Journal of the European Communities L 84/1 of 27 March 1999 and the Annex to the Commission Decision of 18 July 2000 amending Commission Decision 1999/217 / EC on a list of flavoring substances used in or on foods (2000/489 / EC), to be published in the Official Journal of the European Communities L 197/53 of 3 August 2000.
- EC Regulation
- a volatile flavoring agent is preferably understood to be a sensorically active component having a vapor pressure of greater than or equal to 0.01 Pa at 25 ° C., in particular having a vapor pressure of greater than or equal to 0.025 Pa at 25 ° C.
- a majority of the volatile flavorings have a vapor pressure of greater than or equal to 1 Pa at 25 ° C, so that in particular such substances are considered as flavoring agents in the context of the present invention.
- cooling substance is used to designate physiologically effective cooling substances (cooling agents). Cooling substances are regularly used to produce a cool sensory impression on the skin or mucosa, for example on the mucosa in the mouth, nose and / or throat, but in fact no physical cooling takes place, for example in the evaporation of solvents. As cooling substances, both individual components and mixtures can be used. The best known cooling substance is L-menthol.
- flavorings - with or without physiological cooling effect - are both complex natural raw materials such as extracts derived from plants and essential oils, or fractions derived therefrom and uniform substances, as well as uniform synthetic or biotechnologically derived flavorings.
- Examples of natural raw materials are peppermint oils, spearmint oils, mentha arvensis oils, anise oils, clove oils, citrus oils, cinnamon bark oils, wintergreen oils, cassia oils, davana oils, pine needle oils, eucalyptus oils, fennel oils, galbanum oils, ginger oils, camomile oils, cumin oils, rose oils, geranium oils, sage oils, parsley oils , Garlic oils, star anise oils, thyme oils, juniper berry oils, rosemary oils, angelica root oils, and the fractions of these oils.
- uniform flavorings are anethole, menthol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyptol, limonene, eugenol, pinene, sabin hydrate, 3-octanol, carvone, gamma-octalactone, gamma-nonalactone, germacren-D, viridiflorol, 1 , 3E, 5Z-undecatriene, isopulegol, piperone, 2-butanone, ethyl formate, 3-octyl acetate, isoamylisovalerate, isoamyl acetate, isoamyl butyrate, ethyl butyrate, vanillin, ethylvanillin, hexanol, hexanal, cis-3-hexenol, cis-3-hexenyl
- Examples of other flavoring and / or flavoring agents which may be advantageously combined with the tetrahydropyrans of the present invention are substances having a physiological cooling effect, i. Substances that cause cold sensation in the mucous membranes.
- Such cooling agents are in particular I-menthol, I-isopulegol, menthone acetals (eg menthone-glycerol acetal), menthyl esters, esters of menthol and hydroxycarboxylic acids having 2 to 6 carbon atoms (eg menthyl lactate), substituted menthane-3-carboxamides (eg menthan-3-carboxylic acid N-ethylamide), branched alkanecarboxamides (eg 2-isopropyl-N, 2,3-trimethylbutanamide), 3,3,5-trimethylcyclohexanol, 3-menthoxy-1,2-propanediol, 3-menthoxy-2-methyl-1 , 2-propanediol, 2-
- Preferred substances with a physiological cooling effect are menthyl esters, menthone acetals, menthane-3-carboxamides and branched alkanecarboxamides.
- menthyloxamate menthyl N-methyloxamate, menthyl N, N-dimethyloxamate, menthyl N-ethyloxamate, menthyl N, N-diethyloxamate, menthyl N-propyloxamate, menthyl N, N- dipropyloxamate, menthyl N-isopropyloxamate, menthyl N, N-diisopropyloxamate, menthyl N-cyclopropyloxamate, menthyl N-butyloxamate, morpholin-4-yl-oxo-acetic acid (1R, 2S, 5R) -2-isopropyl 5-methylcyclohexyl ester, menthyl N- (2-methoxyethyl) oxamate, menthyl N- (3-methoxypropyl) oxamate, menthyl N- (2-hydroxyeth
- one or more of the flavoring substances without physiological cooling effect are selected from the group consisting of substances which cause a sharp taste or a heat or heat sensation on the skin and mucous membranes or a tingling sensation in the oral and pharyngeal space, in particular paprika, chilli pepper powder, pepper extract, pepper extract, chili pepper extract, ginger root extract, grains of paradise extract (Aframomum melegueta), paracress extract (Jambu oleoresin, Spilanthes acmella or Spilanthes oleracea ), Extracts of Japanese pepper (Zanthoxylum piperitum), extracts of Kaempferia galanga, extracts of Alpinia galanga, extracts of water pepper (Polygonium hydropiper), capsaicin, dihydrocapsaicin, gingerol, Paradol, Shogaol, piperine, Saanshool-I, Saanshool-II, Sanshoamid
- the total amount of the alkylated tetrahydropyrans used according to the invention is preferably 0.5 to 30% by weight, preferably 1 to 20% by weight and more preferably 2 to 10% by weight, based on the total weight of the aroma composition.
- the alkylated tetrahydropyrans according to the invention are present (preferably as constituents of an aroma composition in the abovementioned quantitative ranges), depending on the preparation, generally in such preparations, preferably in a total proportion of from 10 ppm to 2% by weight.
- Preferred is a content of 25 ppm to 1 wt .-%; Particularly preferred is a content of 50 ppm to 0.5 wt .-%, most preferably a content of 100 ppm - 0.25 wt .-%, each based on the total preparation.
- a content of 25 ppm to 1 wt .-% Particularly preferred is a content of 50 ppm to 0.5 wt .-%, most preferably a content of 100 ppm - 0.25 wt .-%, each based on the total preparation.
- further preferred contents are mentioned below.
- flavor or flavor compositions containing the compounds of the invention can be used in pure form, as solutions or in specially prepared form and incorporated into ready-to-use products.
- Suitable solvents are e.g. Ethyl alcohol, 1,2-propylene glycol, glycerin, triacetin, benzyl alcohol and fatty oils such as e.g. Coconut oil or sunflower oil.
- the preparations containing the compounds according to the invention may also contain additives and auxiliaries, in particular preservatives, dyes, antioxidants, flow agents, thickeners, etc.
- the compounds of the invention may be bound to a carrier, spray-dried or encapsulated.
- compounds of the invention may be bound to or in a carrier, e.g. Table salt, sugar, starches or sugar melts.
- the spray-dried form is prepared from the liquid compositions by preparing an emulsion with the addition of certain amounts of a carrier, preferably biopolymers such as starch, modified starches, maltodextrin and gum arabic. This emulsion is dried in spray dryers by very fine distribution with simultaneous temperature application. The result is a powder with the desired loading of liquid composition.
- the encapsulated form is also prepared from the liquid compositions by adding a carrier. There are several technologies that can be used to make capsules.
- the most common are extrusion, spray granulation and coacervation.
- the particle sizes usually range from 10 ⁇ m to 5 mm.
- the most common capsule materials are various starches, maltodextrin and gelatin. These capsules contain the liquid or solid flavor or flavor compositions and can be released by various mechanisms such as heat application, pH shift or chewing pressure.
- formulations containing the compounds according to the invention can advantageously be used above all in oral hygiene products such as toothpastes and mouthwashes, chewing gums, foods such as confectionery and lozenges, stimulants such as tobacco and pharmaceutical preparations and nasal sprays.
- the total content of an aroma composition containing one or more compounds according to the invention in ready-to-use mouthwashes is preferably from 0.01 to 1% by weight, preferably from 0.05 to 0.5% by weight, more preferably from 0.1 to 0.3 Wt .-%, in each case based on the total mouthwash.
- the total content of the aroma composition containing one or more compounds of the invention is preferably 0.1 to 15 wt .-%, preferably, a content of 0.5 to 8 wt .-%, particularly preferably 1 to 5 wt .-%, respectively based on the entire mouthwash concentrate.
- the total content of the aroma composition containing one or more compounds according to the invention is preferably 0.1 to 5% by weight, preferably 0.5 to 2% by weight, particularly preferably 0.8 to 1.5% by weight, in each case based on the total toothpaste.
- the total content of the aroma composition containing one or more compounds according to the invention is preferably from 0.1 to 5% by weight, preferably from 0.5 to 3% by weight, particularly preferably from 0.8 to 2.5% by weight, in each case based on the total chewing gum.
- the total content of the aroma composition containing one or more compounds according to the invention is preferably from 0.01 to 2% by weight, preferably from 0.05 to 1% by weight, more preferably from 0.1 to 0.5% by weight. %, in each case based on the whole lollipop.
- the preparation according to the invention is preferred
- Oral hygiene preparations in particular toothpastes flavored with compositions containing the compounds of the invention, generally consist of an abrasive system (abrasives or abrasives), such as silicic acids, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites, of surfactants , such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or Cocamidopropylbetain, from humectants, such as glycerol and / or sorbitol, thickeners, such as carboxymethylcellulose, polyethylene glycols, carrageenans and / or Laponites ® , from sweeteners, such as saccharin, cooling agents, stabilizers and active ingredients such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichlor
- Chewing gums flavored with the compositions containing the compounds of the invention generally comprise a chewing gum base, ie chewing gum that becomes plastic upon chewing, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols (especially sorbitol, xylitol, mannitol), cooling agents, flavoring agents for unpleasant taste impressions, other flavor modulators for other, usually not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers and stabilizers.
- a chewing gum base ie chewing gum that becomes plastic upon chewing
- sugars of various types, sugar substitutes, other sweet-tasting substances especially sugar alcohols (especially sorbitol, xylitol, mannitol), cooling
- elastomers such as polyvinyl acetates (PVA), polyethylenes, (low or medium molecular weight) polyisobutenes (PIB), polybutadienes, isobutene-isoprene copolymers (butyl rubber), polyvinyl ethyl ether (PVE), Polyvinyl butylene, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rubber, SBR) or vinyl elastomers, for example based on vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate or ethylene /
- SBR styrene-butadiene rubber
- chewing gum bases include other ingredients such as (mineral) fillers, plasticizers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as hydrogenated (hydrogenated) vegetable or animal fats, mono-, di- or triglycerides.
- Suitable (mineral) fillers are, for example, calcium carbonate, titanium dioxide, silica, talc, alumina, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof.
- plasticizers or detackifiers examples include lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate), triethyl citrate.
- Suitable waxes include paraffin waxes, candelilla wax, carnauba wax, microcrystalline waxes and polyethylene waxes.
- Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and diglycerides of fatty acids, for example glycerol monostearate.
- the compounds according to the invention or the compositions containing the compounds according to the invention are particularly particular are suitable for refreshing the respiratory air and neutralizing or reducing bad halitosis.
- oral care products oral hygiene products
- oral hygiene products such as.
- saliva products oral hygiene products
- substances such as triclosan, zinc citrate, sulphate, poly- and pyrophosphates, bicarbonates, strontium and potassium salts, tin pyrophosphate, chloride, aluminum lactate, hydrogen peroxide, fluorides, vitamins, cetylpyridinium chloride and emulsifiers, e.g.
- sweeteners such as e.g. Aspartame, saccharin, acesulfame-K, sorbitol; Xylitol, cyclamates (e.g., sodium cyclamate), sucralose, alitame, neotame, thaumatin, neohesperidin dihydrochalcone, maltitol, lactitol, or chewing gum masses.
- sweeteners such as e.g. Aspartame, saccharin, acesulfame-K, sorbitol; Xylitol, cyclamates (e.g., sodium cyclamate), sucralose, alitame, neotame, thaumatin, neohesperidin dihydrochalcone, maltitol, lactitol, or chewing gum masses.
- Another positive feature of the compounds according to the invention is their stability in chalk or bicarbonate based toothpastes, which are difficult to flavor because of their alkaline pH.
- the compounds according to the invention or the compositions containing the compounds according to the invention are also suitable for use in pharmaceutical preparations, such as. As nasal drops and sprays or Einreibeoniaparaten.
- the compositions containing the compounds according to the invention are suitable for masking the bitter taste of medicaments.
- a pellitorin solution (hereinafter referred to as "pellitorin solution PLM”) consisting of 10% pellitorin (comprising 4.9% 2E, 4Z-decadienoic acid N-isobutylamide and 94.3% 2E, 4E-decadienoic acid N-isobutylamide), 45% propylene glycol and 45% natural peppermint oil ( Mentha arvensis ).
- Example 1.0 Panel examination of a toothpaste sample (13 sensory trained subjects):
- the compounds according to the invention do not change the flavor profile of the aroma; Rather, they enhance its taste impression in the desired manner.
- the impression of freshness and fullness is enhanced and the overall effect of the aroma unfolds better.
- the taste impression is significantly enhanced (descriptors "Freshness during” and "Impact” (overall taste impression 10 seconds after brushing).)
- 9 liked the pattern, which contained the compounds of the invention see. FIG. 1 ).
- the hydrogenation was carried out in a hydrogenation autoclave.
- 202 g of 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran (from the 1st stage) were charged to the autoclave with 8 g of Pd / activated carbon (Pd content: 5%) and hydrogenated at 30 bar hydrogen pressure ,
- Pd content 8 g
- Pd content 8 g
- H 2 uptake was complete after 35 min. 107% H 2 of the theory was recorded.
- the catalyst was filtered off and then rinsed with ethanol.
- the material thus obtained was then distilled over 120 cm column. There were obtained 131 g of 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran (purity> 97%) (73% yield of theory).
- Example 1.2 Preparation of various alkyl- and alkenyl-substituted tetrahydropyrans using the example of 2,2,6-trimethyl-5-isopropyltetrahydropyran
- Example 2.2 Aroma peppermint type Cool
- component I (% by weight) II (% by weight) 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran 4 5 isoamyl 2 2 ethyl butyrate 0.5 - butyl butyrate - 0.5 ethyl vanillin 2 - vanillin - 1
- Frambinone TM [4- (4-hydroxyphenyl) -2-butanone] 0.5 0.5
- I-menthol (of course) 8th 11 triacetin - 80 1,2-propylene glycol 83 -
- the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran causes a marked "boost effect" and mediates - In comparison to the flavor not according to the invention - an increased feeling of freshness, especially in the initial phase of consumption.
- the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran causes an increased feeling of freshness and gives - in comparison to the flavor not according to the invention - a greater mouthfeel, especially at the beginning of chewing.
- component I (% by weight) II (% by weight) Sorbitol 70% 63,00
- Ad 100 Deionized water 11.31 11.31 saccharin 0.20 0.20 Sodium monofluorophosphate 1.14 1.14 Solbrol 0.15 0.15 trisodium phosphate 0.10 0.10 PEG 1500 (PEG 32) 5.00 5.00 Sident 9 (Abrasive Silica) 8.00 8.00 Sident 22 S (thickening silica) 8.00 8.00 sodium 0.60 0.60 sodium lauryl sulfate 1.50 1.50
- Aroma cinnamon type (example 2.8) 1.00 - Aroma wintergreen type Cool (example 2.5) - 1.00
- Pellitorin solution PLM (containing 10% pellitorin) - 0,025
- the paste gains a clearer freshness profile when brushed by the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran and gives - in comparison to the flavor not according to the invention - a clear retronasal Cooling.
- Toothpaste III is particularly suitable as toothpaste for children.
- Example 2.18 Mouthwash ('ready to use' without alcohol) with aroma eucalyptus type
- Example 2.24 Neck Sweets with Liquid-Viscous Core Filling (Center-filled Hard Candy) with Aroma Cinnamon Type and Aroma Cinnamon Type Cool
- Aroma G had the following composition (in each case in wt .-%): 0, 1% neotame powder, 29.3% peppermint oil arvensis, ad 100% peppermint piperita oil Willamette, 2.27% sucralose, 0.7% clove oil ( clove bud oil), 2.28% triacetin, 5.4% diethyl tartrate, 12.1% peppermint oil yakima, 0.7% ethanol, 3.36% 2-hydroxyethylmenthyl carbonate, 2.6% 2-hydroxypropylmenthyl carbonate, 5.77% D-limonene, 5.67% L-menthyl acetate, 0.4% vitamin E acetate.
- the ready-to-consume gelatin capsules I, II, III were prepared according to WO 2004/050069 and each had a diameter of 5 mm, the weight ratio Core material to shell material was 90:10. The capsules each opened in the mouth within less than 10 seconds and completely dissolved within less than 50 seconds.
- Aroma P1 had the following composition (in each case in% by weight):
- the preparation of the chewing gum base K1 and the chewing gum can analogously to US 5,601,858 respectively.
- the preparation of the chewing gum base K2 and the chewing gum can be analogous to US 6,986,907 respectively.
- the chewing gums of the formulas (I) and (II) were made as strips, the recipe (III) as Kompaktate in pillow form and then coated with xylitol.
Abstract
Description
Die vorliegende Erfindung betrifft alkylsubstituierte Tetrahydropyrane der nachfolgenden Formel (I), Mischungen umfassend diese alkylsubstituierten Tetrahydropyrane, deren jeweilige Verwendung und entsprechende aromatisierte Produkte.The present invention relates to alkyl-substituted tetrahydropyrans of the following formula (I), mixtures comprising these alkyl-substituted tetrahydropyrans, their respective use and corresponding aromatized products.
In einer besonderen Ausführungsform betrifft die Erfindung die Verwendung dieser Aromastoffe in Aroma- und Geschmacksstoffkompositionen mit Frischewirkung für den Einsatz in Mundhygieneprodukten.In a particular embodiment, the invention relates to the use of these flavorings in aroma and flavor compositions having a fresh effect for use in oral hygiene products.
Die Erfindung betrifft desweiteren Zubereitungen und Rhinologica, die im Bereich des Mundes, des Rachens und der Atemwege ein frisches und befreiendes Gefühl hervorrufen und Zubereitungen, die diese Verbindungen enthalten.The invention further relates to preparations and rhinologica which cause a fresh and liberating sensation in the area of the mouth, throat and respiratory tract and preparations containing these compounds.
Um dem Bedarf des Verbrauchers nach immer neuen Geruchs- und Geschmackserlebnissen nachzukommen, besteht in der Aromen- und Geschmacksstoffindustrie ein großer Bedarf an Stoffen, die herausragende sensorische (d.h. mit den Sinnen wahrnehmbare) Eigenschaften besitzen und mit denen sich bemerkenswerte neuartige Effekte erzielen lassen. Dabei können neben den reinen geruchlichen und geschmacklichen Eigenschaften weitere zusätzliche Eigenschaften von Bedeutung sein, so z.B. dass die Geruchs- und Geschmacksempfindungen gehemmt oder verstärkt werden.In order to meet the consumer's need for ever-new odor and taste experiences, there is a great need in the flavor and flavor industry for fabrics that have outstanding sensory (ie sensory) properties and can produce remarkable novel effects. Besides the pure odor and taste properties other additional properties of importance, such as that the odor and taste sensations are inhibited or enhanced.
Aroma-, bzw. Geschmacksstoffkompositionen mit Frischewirkung verleihen z.B. Mundhygieneprodukten, wie Zahnpasten und Mundwässern, und Süßwaren wie Bonbons und Kaugummis, ihren typischen, frischen und als angenehm empfundenen Geschmack.Flavoring or flavoring compositions with freshness effect impart e.g. Oral hygiene products, such as toothpastes and mouthwashes, and sweets such as sweets and chewing gum, their typical, fresh and pleasant taste.
Stoffe, die in großem Umfang für die Herstellung solcher Aroma-, bzw. Geschmacksstoffkompositionen mit Frischewirkung verwendet werden, sind beispielsweise Eucalyptol (1,8-Cineol) und Menthol. Die Verwendung dieser Stoffe ist jedoch mit einigen Nachteilen behaftet. So zeigt das Eucalyptol neben seiner Frischewirkung einen sehr starken medizinischen Eigengeschmack, der von vielen Konsumenten als abstoßend empfunden wird, besonders wenn das Eucalyptol in höheren Dosierungen verwendet wird. Bei der Verwendung von Menthol setzt die Frischewirkung mit einer gewissen Verzögerung ein, und bei höheren Dosierungen entwickelt das Menthol einen bitter-scharfen Eigengeschmack, der eine eher unangenehme Wirkung hat.Substances that are widely used for the preparation of such fresh flavoring or flavoring compositions include eucalyptol (1,8-cineole) and menthol. The use of these substances, however, has some disadvantages. Thus, in addition to its freshness, Eucalyptol has a very strong medicinal taste, which many consumers find repulsive, especially when Eucalyptol is used in higher doses. With the use of menthol, the freshness effect begins with a certain delay, and at higher dosages the menthol develops a bitter-sharp taste, which has a rather unpleasant effect.
Es war daher die primäre Aufgabe der vorliegenden Erfindung, Verbindungen bzw. Gemische von Verbindungen anzugeben, die in Aroma- und/oder Geschmacksstoffkompositionen mit Frischewirkung zu einem verstärkten, schnell wahrnehmbaren Frischeerlebnis führen. Darüber hinaus sollten die anzugebenden Verbindungen bzw. Verbindungsgemische vorzugsweise einen möglichst schwachen Eigengeschmack zeigen, insbesondere wenig oder gar nicht medizinisch und/oder bitter schmecken.It was therefore the primary object of the present invention to provide compounds or mixtures of compounds which result in flavor and / or flavor compositions with freshness effect to an intensified, quickly perceptible freshness experience. In addition, the compounds or mixtures of compounds to be indicated should preferably have the lowest possible intrinsic taste, especially little or no medicinal and / or bitter taste.
Die erfindungsgemäßen neuen Tetrahydropyrane zeigen eine dem 1,8-Cineol (Eucalyptol) verwandte Wirkung in Bezug auf ein frisches befreiendes Gefühl im Mund, Rachenraum und den Atemwegen zu erzielen, ohne dabei ein unangenehmes Geschmacksempfinden zu erzeugen.The novel tetrahydropyrans according to the invention exhibit an effect related to the 1,8-cineol (eucalyptol) with respect to a fresh liberating sensation in the mouth, pharynx and respiratory tract, without producing an unpleasant taste sensation.
Die erfindungsgemäßen Tetrahydropyrane zeichnen sich im wesentlichen durch einen neutralen, frisch-kühlen Geschmack aus. Sie eignen sich deshalb hervorragend dazu, in Aroma- und Geschmacksstoffkompositionen eingesetzt zu werden. Bemerkenswert ist ihre Fähigkeit, in Aroma- und Geschmacksstoffkompositionen die Intensität und die Kraft des Frische-Gefühls zu steigern.The tetrahydropyrans according to the invention are distinguished essentially by a neutral, fresh-cool taste. They are therefore ideal for use in flavor and flavor compositions. Noteworthy is their ability to increase in aroma and flavor compositions, the intensity and the power of freshness feeling.
Die Wirkung, ein frisches befreiendes Gefühl im Mund, Rachenraum und den Atemwegen hervorzurufen, trifft bei den erfindungsgemäßen alkylierten Tetrahydropyranen auf alle isomeren Formen, d. h. Diastereomere und Enantiomere zu.The effect of producing a fresh liberating sensation in the mouth, pharynx, and respiratory tract, in the alkylated tetrahydropyrans of the present invention, applies to all isomeric forms, i. H. Diastereomers and enantiomers too.
Erfindungsgemäß wird deshalb ein alkyliertes Tetrahydropyran der Formel (I) angegeben:
jedes R1 unabhängig voneinander entweder
Wasserstoff
oder ein verzweigter oder unverzweigter Alkylrest mit 1 bis 3 C-Atomen
oder ein verzweigter oder unverzweigter Alkenylrest mit 2 bis 3 C-Atomen,
und R2 ein verzweigter oder unverzweigter Alkyl oder Alkenylrest mit 3 bis 4 C-Atomen
und R3 ein verzweigter oder unverzweigter Alkylrest mit 1 bis 5 C-Atomen ist,
ausgenommen
2,6-Dimethyl-3-(1-methylethenyl)-tetrahydropyran (CA5-Nr 1008981-43-8):
each R1 independently either
hydrogen
or a branched or unbranched alkyl radical having 1 to 3 C atoms
or a branched or unbranched alkenyl radical having 2 to 3 C atoms,
and R 2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms
and R 3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
except
2,6-Dimethyl-3- (1-methylethenyl) tetrahydropyran (CA5 No. 1008981-43-8):
Alkylierte Tetrahydropyranderivate sind als sensorisch aktive Substanzen unter anderem beispielsweise in
Als Aromastoffe finden aus dieser Strukturklasse vor allen Dingen Rosenoxid [2-(2-Methyl-1-propenyl)-4-methyltetrahydropyran, CAS-Nr 16409-43-1; FEMA-Nr 3236] und Limetol (2-Vinyl-2,6,6-trimethyltetrahydropyran, CAS-Nr 7392-19-0; FEMA-Nr 3735) Verwendung; für Limetol beispielsweise beschrieben in
Für den Mundhygienebereich sind geschmacksmodulierende Substanzen bekannt; so werden in
Ebenfalls aromaintensivierende Eigenschaften besitzen die in
Innerhalb der Gruppe erfindungsgemäßer Verbindungen und von Mischungen bestehend aus oder enthaltend zwei, drei, vier oder mehr der Verbindungen sind bestimmte alkylierte Tetrahydropyrane bevorzugt. Bevorzugt ist es insbesondere, wenn die Verbindung bzw. eine der Verbindungen ausgewählt ist aus solchen alkylierten Tetrahydropyranen der Formel (I), bei denen
jedes R1 unabhängig voneinander ein Methyl-, Ethyl- oder Vinylrest ist,
R2 ein Isopropyl-, Isopropenyl-, sec-Butyl- oder sec-Butenylrest ist, und
R3 ein unverzweigter Alkylrest mit 1 bis 3 C-Atomen ist.Within the group of compounds according to the invention and of mixtures consisting of or containing two, three, four or more of the compounds, certain alkylated tetrahydropyrans are preferred. It is particularly preferred if the compound or one of the compounds is selected from those alkylated tetrahydropyrans of the formula (I) in which
each R1 is independently a methyl, ethyl or vinyl radical,
R 2 is isopropyl, isopropenyl, sec-butyl or sec-butenyl, and
R3 is an unbranched alkyl radical having 1 to 3 carbon atoms.
Hierbei ist die Verbindung bzw. zumindest eine der Verbindungen der Mischung bevorzugt ein solches alkyliertes Tetrahydropyran, bei dem
jedes R1 unabhängig voneinander ein Methyl- oder Ethylrest ist,
R2 ein Isopropyl- oder sec-Butylrest ist, und
R3 ein Methyl- oder Ethylrest ist.Here, the compound or at least one of the compounds of the mixture is preferably such an alkylated tetrahydropyran in which
each R1 is independently a methyl or ethyl radical,
R2 is an isopropyl or sec-butyl radical, and
R3 is a methyl or ethyl radical.
Vorzugsweise ist die Verbindung bzw. eine der Verbindungen der Mischung ausgewählt aus der Gruppe bestehend aus 2,6-Diethyl-5-isopropyl-2-methyltetrahydropyran, 6-Ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran, 2,6-Dimethyl-5-isopropyl-2-ethyltetrahydropyran, 2,6-Dimethyl-5-isopropenyl-2-vinyltetrahydropyran, 2,6-Diethyl-5-sec.-butyl-2-methyltetrahydropyran und 2,6-Dimethyl-5-sec.-butyl-2-ethyltetrahydropyran.Preferably, the compound or one of the compounds of the mixture is selected from the group consisting of 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran, 2.6 Dimethyl 5-isopropyl-2-ethyltetrahydropyran, 2,6-dimethyl-5-isopropenyl-2-vinyltetrahydropyran, 2,6-diethyl-5-sec-butyl-2-methyltetrahydropyran, and 2,6-dimethyl-5- sec-butyl-2-ethyltetrahydropyran.
Eine ganz besonders bevorzugte Verbindung zum Lösen der Aufgabe der Erfindung ist 2,6-Diethyl-5-isopropyl-2-methyltetrahydropyran; entsprechend bevorzugt sind auch erfindungsgemäße Mischungen enthaltend zumindest diese Verbindung.A most preferred compound for achieving the object of the invention is 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran; correspondingly preferred are also mixtures according to the invention containing at least this compound.
Die Erfindung beruht auf der überraschenden Erkenntnis, dass erfindungsgemäße alkylierte Tetrahydropyrane die Frischewirkung von Aromakompositionen (Kompositionen enthaltend einen oder mehrere Aromastoffe und/oder Geschmacksstoffe) mit Frischewirkung schnell wahrnehmbar verstärken, ohne jedoch einen starken Eigengeschmack aufzuweisen.The invention is based on the surprising finding that alkylated tetrahydropyrans according to the invention quickly increase the fresh effect of aroma compositions (compositions containing one or more flavorings and / or flavorings) with a fresh effect without, however, having a strong intrinsic taste.
Die erfindungsgemäßen Mischungen bestehen aus zwei, drei, vier oder mehr Verbindungen der Formel (I), vorzugsweise jeweils in einer der vorstehend als bevorzugt angegebenen Ausgestaltungen. Des Weiteren bevorzugt ist es, wenn in einer erfindungsgemäß zu verwendenden Mischung nicht nur eine vorstehend als besonders bevorzugt bezeichnete Verbindung der Formel (I) vorhanden ist, d. h. nicht nur eine Verbindung, die eine, mehrere oder ausschließlich besonders bevorzugte Gruppen R1, R2 und R3 umfasst, sondern zwei oder mehr als besonders bevorzugte erfindungsgemäße Verbindungen der Formel (I). Vorzugsweise sind somit zwei, drei oder sämtliche Verbindungen in einer erfindungsgemäßen Mischung bestehend aus Verbindungen der Formel (I) aus der Gruppe der als bevorzugt bezeichneten Verbindungen ausgewählt.The mixtures according to the invention consist of two, three, four or more compounds of the formula (I), preferably in each case in one of the embodiments given above as being preferred. It is furthermore preferred if, in a mixture to be used according to the invention, not only one compound of the formula (I) described above as being particularly preferred is present, d. H. not only a compound which comprises one, several or exclusively particularly preferred groups R 1, R 2 and R 3, but two or more particularly preferred compounds of the formula (I) according to the invention. Preferably, therefore, two, three or all compounds in a mixture according to the invention consisting of compounds of the formula (I) are selected from the group of compounds designated as preferred.
Die Verbindungen der Formel (I) können gemäß den dem Fachmann bekannten Herstellungsmethoden erhalten werden. Beispielsweise können die Verbindungen der Formel (I) in einem Verfahren hergestellt werden, wie in dem nachfolgenden Schema verdeutlicht ist. Die Umsetzung des Aldehyds (B) mit der Alkoholkomponente (A) führt zu dem entsprechenden cyclisierten Tetrahydropyranverbindung (C), welches unter Formel (I) zu subsumieren ist. Tetrahydropyranverbindung (C) kann optional in einem zweiten Reaktionsschritt zu der Tetrahydropyranverbindung (D) reduziert werden, welche ebenfalls unter Formel (I) zu subsumieren ist.
R1 und R3 jeweils die oben genannte (gegebenenfalls bevorzugte) Bedeutung haben, und
Ra, Rb und Rc unabhängig voneinander Wasserstoff, Methyl oder Ethyl darstellen,
mit der Maßgabe, dass Ra, Rb und Rc in Summe 1 oder 2 C-Atome enthalten, d.h. dass die Reste Ra, Rb und Rc zusammen mit den beiden mit #-markierten CH-Resten insgesamt dem Rest R2 in Formel (I) entsprechen.The compounds of the formula (I) can be obtained according to the preparation methods known to the person skilled in the art. For example, the compounds of formula (I) can be prepared in a process as illustrated in the scheme below. The reaction of the aldehyde (B) with the alcohol component (A) leads to the corresponding cyclized tetrahydropyran compound (C), which is to be subsumed under formula (I). Tetrahydropyran compound (C) may optionally be reduced in a second reaction step to the tetrahydropyran compound (D) which is also to be subsumed under formula (I).
R1 and R3 each have the above-mentioned (optionally preferred) meaning, and
R a , R b and R c independently of one another represent hydrogen, methyl or ethyl,
with the proviso that R a , R b and R c in total contain 1 or 2 C atoms, ie that the radicals R a , R b and R c together with the two with #-labeled CH radicals total of the radical R 2 in formula (I).
Die Umsetzung von Alkohol (A) mit Aldehyd (B) erfolgt vorzugsweise in Gegenwart saurer Katalysatoren. Als saure Katalysatoren können z.B. anorganische Säuren wie Phosphorsäure, Polyphosphorsäure, Salzsäure, Salpetersäure, Schwefelsäure, organische Säuren wie Methansulfonsäure, Toluolsulfonsäure oder Trifluoressigsäure eingesetzt werden. Daneben können auch feste Säuren wie saure Ionentauscher, saure Aluminosilicate oder saure Zeolithe verwendet werden.The reaction of alcohol (A) with aldehyde (B) is preferably carried out in the presence of acidic catalysts. As acid catalysts, e.g. inorganic acids such as phosphoric acid, polyphosphoric acid, hydrochloric acid, nitric acid, sulfuric acid, organic acids such as methanesulfonic acid, toluenesulfonic acid or trifluoroacetic acid can be used. In addition, solid acids such as acidic ion exchangers, acidic aluminosilicates or acidic zeolites can also be used.
Weitere bevorzugte saure Katalysatoren sind Lewis-Säuren wie beispielsweise AlX3, ZnX2, FeX3, TiX4, wobei X für ein Halogenid aus der Gruppe Chlor, Brom oder Iod steht, sowie BF3, insbesondere AlCl3, ZnCl2, FeCl3, TiCl4 sowie BF3-Addukte.Further preferred acidic catalysts are Lewis acids such as AlX 3 , ZnX 2 , FeX 3 , TiX 4 , wherein X is a halide from the group chlorine, bromine or iodine, and BF 3 , in particular AlCl 3 , ZnCl 2 , FeCl 3 , TiCl 4 and BF 3 adducts.
Besonders bevorzugte Katalysatoren sind Schwefelsäure, Phosphorsäure und BF3-Addukte, insbesondere BF3-Etherat.Particularly preferred catalysts are sulfuric acid, phosphoric acid and BF 3 adducts, in particular BF 3 etherate.
Das molare Verhältnis von Alkohol (A) zu Aldehyd (B) liegt bevorzugt im Bereich von 1 : 5 bis 1 : 3, besonders bevorzugt im Bereich von 1 : 3 bis 1 : 1. Insbesondere bevorzugt ist ein molares Verhältnis von Alkohol (A) zu Aldehyd (B) von 1 zu 1,05 - 1,2 (d.h. leichter Überschuss an Aldehyd).The molar ratio of alcohol (A) to aldehyde (B) is preferably in the range from 1: 5 to 1: 3, particularly preferably in the range from 1: 3 to 1: 1. Particularly preferred is a molar ratio of alcohol (A) to aldehyde (B) of 1 to 1.05-1.2 (ie, slight excess of aldehyde).
Die Reaktionstemperatur liegt vorzugsweise im Bereich von -20°C bis 50°C, bevorzugt im Bereich von -10°C bis 40°C und insbesonders bevorzugt im Bereich von 0°C bis 15°C.The reaction temperature is preferably in the range of -20 ° C to 50 ° C, preferably in the range of -10 ° C to 40 ° C, and more preferably in the range of 0 ° C to 15 ° C.
Besonders bevorzugt ist bei der Umsetzung von (A) mit (B) folgendes Temperaturprofil: zunächst erfolgt die Reaktion der Alkoholkomponente (A) mit der Aldehydkomponente (B) in der Kälte (vorzugsweise bei 0 - 10°C). Im Falle der Katalyse mit einer Protonensäure folgt vorzugsweise anschließend ein Erwärmen der Reaktionsmischung auf etwa 60 - 80°C, um eine möglichst vollständige Umsetzung zu erreichen. Ein solches anschließendes Erwärmen kann bei Katalyse mit einer Lewissäure hingegen entfallen.In the reaction of (A) with (B), the following temperature profile is particularly preferred: first, the reaction of the alcohol component (A) with the aldehyde component (B) takes place in the cold (preferably at 0-10 ° C.). In the case of catalysis with a protic acid, the reaction mixture is then preferably subsequently heated to about 60-80 ° C. in order to achieve as complete a conversion as possible. However, such subsequent heating may be omitted in catalysis with a Lewis acid.
Verbindungen der Formel (D), dabei insbesondere solche Verbindungen der Formel (I), die keine C-C-Doppelbindungen aufweisen, können mittels Reduktion aus den entsprechenden ungesättigten Verbindungen der Formel (C) erhalten werden, vorzugsweise mittels Hydrierung an Hydrierkatalysatoren in einer Wasserstoffatmosphäre.Compounds of the formula (D), in particular those compounds of the formula (I) which have no C-C double bonds, can be obtained by reduction from the corresponding unsaturated compounds of the formula (C), preferably by hydrogenation over hydrogenation catalysts in a hydrogen atmosphere.
Als Hydrierkatalysatoren zur Reduktion der in Verbindungen der Formel (C) vorhandenen C-C-Doppelbindung(en) eignen sich beispielsweise Elemente der 8. Nebengruppe des Periodensystems. Besonders vorteilhaft sind hier die Elemente Nickel, Palladium, Platin, Rhodium, Iridium, Ruthenium sowie deren Mischungen, Verbindungen und Legierungen. Diese Katalysatoren können, vorzugsweise in elementarer und fein verteilter Form, aufgebracht auf Träger oder zusammen mit anderen Metallen oder deren Verbindungen, eingesetzt werden. Als vorteilhafte Trägermaterialen seien genannt Aktivkohle, Aluminiumoxide, Metalloxide, Kieselgele, Zeolithe, Tone, Tongranulate, amorphe Aluminiumsilicate, oder sonstige anorganische oder polymere Träger.Suitable hydrogenation catalysts for reducing the C-C double bond (s) present in compounds of the formula (C) are, for example, elements of the 8th subgroup of the Periodic Table. Particularly advantageous here are the elements nickel, palladium, platinum, rhodium, iridium, ruthenium and mixtures thereof, compounds and alloys. These catalysts can be applied, preferably in elemental and finely divided form, to carriers or together with other metals or their compounds. Preferred support materials include activated carbon, aluminum oxides, metal oxides, silica gels, zeolites, clays, clay granules, amorphous aluminum silicates, or other inorganic or polymeric supports.
Der Wasserstoffdruck bei der Hydrierungsreaktion liegt im Bereich von 1 bis 200 bar, bevorzugt im Bereich von 1 bis 100 bar, insbesondere bevorzugt im Bereich von 5 bis 50 bar.The hydrogen pressure in the hydrogenation reaction is in the range of 1 to 200 bar, preferably in the range of 1 to 100 bar, particularly preferably in the range of 5 to 50 bar.
Verbindungen der Formel (I) können nach üblichen Methoden, z.B. durch Destillation, gereinigt werden.Compounds of formula (I) may be prepared by conventional methods, e.g. by distillation.
Zur Erzielung von frischen, etherischen, minzigen, kühlenden, süßlichen und fruchtigen Geschmacksnoten in Verbindung mit einem frischen befreienden Gefühl im Mund, Rachenraum und den Atemwegen können die erfindungsgemäßen Tetrahydropyrane in reiner Form, miteinander oder aber in einer besonders bevorzugten Form mit Aroma- und/oder Geschmacksstoffen kombiniert werden.To obtain fresh, ethereal, minty, cooling, sweetish and fruity notes in connection with a fresh liberating sensation in the mouth, pharynx and the respiratory tract, the tetrahydropyrans according to the invention can be administered in pure form, combined with each other or in a particularly preferred form with flavoring and / or flavoring agents.
Bevorzugt sind deshalb auch Mischungen umfassend oder bestehend aus
- a) einem, zwei, drei, vier oder mehr erfindungsgemäßen alkylierten Tetrahydropyranen,
- b) einem oder mehreren (flüchtigen) Aroma- und/oder Geschmacksstoffen, insbesondere einer oder mehreren Substanz(en) ausgewählt aus der Gruppe bestehend aus Substanzen mit physiologischer Kühlwirkung, Aromastoffe ohne physiologische Kühlwirkung, trigeminal oder mundwässernd wirksame Substanzen ohne physiologische Kühlwirkung, und geschmacksmodulierende Substanzen,
- c) und optional einem kosmetisch oder pharmazeutisch akzeptablen Träger.
- a) one, two, three, four or more alkylated tetrahydropyrans according to the invention,
- b) one or more (volatile) flavoring and / or flavoring substances, in particular one or more substance (s) selected from the group consisting of substances with physiological cooling effect, flavorings without physiological cooling effect, trigeminal or watering agents without physiological cooling effect, and taste modulating substances
- c) and optionally a cosmetically or pharmaceutically acceptable carrier.
Der Begriff Aromastoff(e) wird in der vorliegenden Erfindung im engeren Sinne entsprechend der Richtlinie des Rates 88/388/EWG vom 22. Juni 1988, veröffentlicht im ABI. L 184 vom 15. Juli 1988, S. 61 verwendet. Aromastoffe sind nach dieser Richtlinie:The term flavoring agent (s) is used in the present invention in the strict sense of Council Directive 88/388 / EEC of 22 June 1988, published in OJ. L 184 of 15 July 1988, p. 61. Flavorings are according to this guideline:
"Definierte chemische Stoffe mit Aromaeigenschaften, die wie folgt gewonnen werden:
- i) durch geeignete physikalische Verfahren (einschließlich Destillation und Extraktion mit Lösungsmitteln) oder enzymatische bzw. mikrobiologische Verfahren aus Stoffen pflanzlichen oder tierischen Ursprungs, die als solche verwendet oder mittels herkömmlicher Lebensmittelzubereitungsverfahren (einschließlich Trocknen, Rösten und Fermentierung) für den menschlichen Verzehr verarbeitet werden;
- ii) durch chemische Synthese oder durch Isolierung mit chemischen Verfahren, wobei ihre chemische Beschaffenheit mit einer Substanz identisch ist, die in einem Stoff pflanzlichen oder tierischen Ursprungs im Sinne von Ziffer i) natürlich vorkommt;
- iii) durch chemische Synthese, wobei jedoch ihre chemische Beschaffenheit nicht mit einer Substanz identisch ist, die in einem Stoff pflanzlichen oder tierischen Ursprungs im Sinne von Ziffer i) natürlich vorkommt."
- (i) by appropriate physical processes (including distillation and solvent extraction) or enzymatic or microbiological processes of substances of plant or animal origin used as such or processed for human consumption by conventional food preparation processes (including drying, roasting and fermentation);
- (ii) by chemical synthesis or by isolation by chemical processes, the chemical nature of which is identical to that of a substance naturally occurring in a substance of plant or animal origin referred to in (i);
- (iii) by chemical synthesis, except that its chemical nature is not identical to a substance naturally occurring in a substance of plant or animal origin referred to in (i). "
Beispiele erfindungsgemäß einzusetzender Aromastoffe sind aufgelistet in den Abschnitten 1 bis 3 der Entscheidung der Kommission vom 23. Februar 1999 über ein Verzeichnis der in oder auf Lebensmitteln verwendeten Aromastoffe, das gemäß Verordnung (EG) Nr. 2232/96 des Europäischen Parlaments und des Rates vom 28. Oktober 1996 erstellt wurde (1999/217/EG), einzusehen im Amtsblatt der Europäischen Gemeinschaften L 84/1 vom 27. März 1999 sowie im Anhang der Entscheidung der Kommission vom 18. Juli 2000 zur Änderung der Entscheidung 1999/217/EG der Kommission über ein Verzeichnis der in oder auf Lebensmitteln verwendeten Aromastoffe (2000/489/EG), einzusehen im Amtsblatt der Europäischen Gemeinschaften L 197/53 vom 3. August 2000.Examples of flavorings to be used according to the invention are listed in Sections 1 to 3 of the Commission Decision of 23 February 1999 on a list Flavorings used in or on foodstuffs prepared in accordance with Regulation (EC) No 2232/96 of the European Parliament and of the Council of 28 October 1996 (1999/217 / EC), to be published in the Official Journal of the European Communities L 84/1 of 27 March 1999 and the Annex to the Commission Decision of 18 July 2000 amending Commission Decision 1999/217 / EC on a list of flavoring substances used in or on foods (2000/489 / EC), to be published in the Official Journal of the European Communities L 197/53 of 3 August 2000.
Unter einem flüchtigen Aromastoff wird im Rahmen der vorliegenden Erfindung vorzugsweise eine sensorisch wirksame Komponente mit einem Dampfdruck von größer oder gleich 0,01 Pa bei 25°C, insbesondere mit einem Dampfdruck von größer oder gleich 0,025 Pa bei 25°C, verstanden. Ein Großteil der flüchtigen Aromastoffe weist einen Dampfdruck von größer oder gleich 1 Pa bei 25°C auf, so dass im Speziellen solche Stoffe als Aromastoffe im Sinne der vorliegenden Erfindung angesehen werden.In the context of the present invention, a volatile flavoring agent is preferably understood to be a sensorically active component having a vapor pressure of greater than or equal to 0.01 Pa at 25 ° C., in particular having a vapor pressure of greater than or equal to 0.025 Pa at 25 ° C. A majority of the volatile flavorings have a vapor pressure of greater than or equal to 1 Pa at 25 ° C, so that in particular such substances are considered as flavoring agents in the context of the present invention.
Nachfolgend wird insbesondere der Begriff "Kühlsubstanz" zur Bezeichnung von physiologisch wirksamen Kühlsubstanzen (Kühlwirkstoffen) verwendet. Kühlsubstanzen werden regelmäßig eingesetzt, um einen kühlen sensorischen Eindruck auf der Haut bzw. Schleimhaut, zum Beispiel auf der Schleimhaut im Mund-, Nasen- und/oder Rachenraum hervorzurufen, wobei allerdings tatsächlich keine physikalische Abkühlung wie zum Beispiel bei der Verdunstung von Lösungsmitteln stattfindet. Als Kühlsubstanzen können sowohl Einzelkomponenten als auch Gemische verwendet werden. Die bekannteste Kühlsubstanz ist L-Menthol.In the following, in particular the term "cooling substance" is used to designate physiologically effective cooling substances (cooling agents). Cooling substances are regularly used to produce a cool sensory impression on the skin or mucosa, for example on the mucosa in the mouth, nose and / or throat, but in fact no physical cooling takes place, for example in the evaporation of solvents. As cooling substances, both individual components and mixtures can be used. The best known cooling substance is L-menthol.
Als weitere Aromastoffe - mit oder ohne physiologische Kühlwirkung - eignen sich sowohl komplexe natürliche Rohstoffe wie aus Pflanzen gewonnene Extrakte und etherische Öle, bzw. daraus gewonnene Fraktionen und einheitliche Stoffe, als auch einheitliche synthetisch oder biotechnologisch gewonnene Aromastoffe.Further flavorings - with or without physiological cooling effect - are both complex natural raw materials such as extracts derived from plants and essential oils, or fractions derived therefrom and uniform substances, as well as uniform synthetic or biotechnologically derived flavorings.
Beispiele für natürliche Rohstoffe sind Pfefferminzöle, Krauseminzöle, Mentha-Arvensis-Öle, Anisöle, Nelkenöle, Citrusöle, Zimtrindenöle, Wintergrünöle, Cassiaöle, Davanaöle, Fichtennadelöle, Eucalyptusöle, Fenchelöle, Galbanumöle, Ingweröle, Kamillenöle, Kümmelöle, Rosenöle, Geraniumöle, Salbeiöle, Petersilienöle, Scharfgarbenöle, Sternanisöle, Thymianöle, Wacholderbeeröle, Rosmarinöle, Angelikawurzelöle, und die Fraktionen dieser Öle.Examples of natural raw materials are peppermint oils, spearmint oils, mentha arvensis oils, anise oils, clove oils, citrus oils, cinnamon bark oils, wintergreen oils, cassia oils, davana oils, pine needle oils, eucalyptus oils, fennel oils, galbanum oils, ginger oils, camomile oils, cumin oils, rose oils, geranium oils, sage oils, parsley oils , Garlic oils, star anise oils, thyme oils, juniper berry oils, rosemary oils, angelica root oils, and the fractions of these oils.
Beispiele für einheitliche Aromastoffe sind Anethol, Menthol, Menthon, Isomenthon, Menthylacetat, Menthofuran, Mintlacton, Eucalyptol, Limonen, Eugenol, Pinen, Sabinenhydrat, 3-Octanol, Carvon, gamma-Octalacton, gamma-Nonalacton, Germacren-D, Viridiflorol, 1,3E,5Z-Undecatrien, Isopulegol, Piperiton, 2-Butanon, Ethylformiat, 3-Octylacetat, Isoamylisovalerianat, Isoamylacetat, Isoamylbutyrat, Ethylbutyrat, Vanillin, Ethyvanillin, Hexanol, Hexanal, cis-3-Hexenol, cis-3-Hexenylacetat, Linalool, alpha-Terpineol, cis- und trans-Carvylacetat, p-Cymol, Damascenon, Damascone, Rosenoxid, Dimethylsulfid, Fenchol, Acetaldehyddiethylacetal, cis-4-Heptenal, Isobutyraldehyd, Isovaleraldehyd, cis-Jasmon, Anisaldehyd, Methylsalicylat, Myrtenylacetat, 2-Phenylethylalkohol, 2-Phenylethylisobutyrat, 2-Phenylethylisovalerat, Zimtaldehyd, Geraniol, Nerol. Bei chiralen Verbindungen können die Aromastoffe als Racemat oder als einzelnes Enantiomer oder als enantiomerenangereichertes Gemisch vorliegen.Examples of uniform flavorings are anethole, menthol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyptol, limonene, eugenol, pinene, sabin hydrate, 3-octanol, carvone, gamma-octalactone, gamma-nonalactone, germacren-D, viridiflorol, 1 , 3E, 5Z-undecatriene, isopulegol, piperone, 2-butanone, ethyl formate, 3-octyl acetate, isoamylisovalerate, isoamyl acetate, isoamyl butyrate, ethyl butyrate, vanillin, ethylvanillin, hexanol, hexanal, cis-3-hexenol, cis-3-hexenyl acetate, linalool , alpha-terpineol, cis- and trans -carvylacetate, p-cymene, damascenone, damascone, rose oxide, dimethyl sulfide, fenchol, acetaldehyde diethyl acetal, cis-4-heptenal, isobutyraldehyde, isovaleraldehyde, cis-jasmone, anisaldehyde, methyl salicylate, myrtenyl acetate, 2- Phenylethyl alcohol, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, cinnamaldehyde, geraniol, nerol. For chiral compounds, the flavoring agents may be present as a racemate or as a single enantiomer or as an enantiomerically enriched mixture.
Beispiele für weitere Aroma- und/oder Geschmacksstoffe, die vorteilhaft mit den erfindungsgemäßen Tetrahydropyranen kombiniert werden können, sind Stoffe mit einer physiologischen Kühlwirkung, d.h. Stoffe, die in den Schleimhäuten eine Kältempfindung hervorrufen. Solche Kühlwirkstoffe sind insbesondere I-Menthol, I-Isopulegol, Menthonacetale (z.B. Menthonglycerinacetal), Menthylester, Ester aus Menthol und Hydroxycarbonsäuren mit 2 bis 6 C-Atomen (z.B. Menthyllactat), substituierte Menthan-3-carbonsäureamide (z.B. Menthan-3-carbonsäure-N-ethylamid), verzweigte Alkancarbonsäureamide (z.B. 2-Isopropyl-N,2,3-trimethylbutanamid), 3,3,5-Trimethylcyclohexanol, 3-Menthoxy-1,2-propandiol, 3-Menthoxy-2-methyl-1,2-propandiol, 2-Menthoxyethanol, 2-Menthoxypropanol, 3-Menthoxypropanol, 4-Menthoxybutanol, 2-Hydroxyethylmenthylcarbonat, 2-Hydroxypropylmenthylcarbonat, Glycerinmenthylcarbonat, N-Acetylglycinmenthylester, Menthylhydroxycarbonsäureester (z.B. Menthyl-3-hydroxybutyrat), Menthan-3,8-diol, Menthyl-2-methoxyacetat, Menthyl-2-(2-methoxyethoxy)acetat, Menthylmonosuccinat, 2-Mercaptocyclodecanon, Menthyl-2-pyrrolidin-5-oncarboxylat.Examples of other flavoring and / or flavoring agents which may be advantageously combined with the tetrahydropyrans of the present invention are substances having a physiological cooling effect, i. Substances that cause cold sensation in the mucous membranes. Such cooling agents are in particular I-menthol, I-isopulegol, menthone acetals (eg menthone-glycerol acetal), menthyl esters, esters of menthol and hydroxycarboxylic acids having 2 to 6 carbon atoms (eg menthyl lactate), substituted menthane-3-carboxamides (eg menthan-3-carboxylic acid N-ethylamide), branched alkanecarboxamides (eg 2-isopropyl-N, 2,3-trimethylbutanamide), 3,3,5-trimethylcyclohexanol, 3-menthoxy-1,2-propanediol, 3-menthoxy-2-methyl-1 , 2-propanediol, 2-menthoxyethanol, 2-menthoxypropanol, 3-menthoxypropanol, 4-menthoxybutanol, 2-hydroxyethylmenthylcarbonate, 2-hydroxypropylmenthylcarbonate, glycerinmenthylcarbonate, N-acetylglycinementhylester, menthylhydroxycarboxylic acid ester (eg, menthyl-3-hydroxybutyrate), menthan-3,8 -diol, menthyl-2-methoxyacetate, menthyl-2- (2-methoxyethoxy) -acetate, menthylmonosuccinate, 2-mercaptocyclodecanone, menthyl-2-pyrrolidin-5-one-carboxylate.
Weitere Beispiele für Stoffe mit einer physiologischen Kühlwirkung, d.h. Stoffe, die in den Schleimhäuten eine Kältempfindung hervorrufen, die vorteilhaft mit den erfindungsgemäßen Tetrahydropyranen kombiniert werden können, finden sich in
Bevorzugte Stoffe mit einer physiologischen Kühlwirkung sind Menthylester, Menthonacetale, Menthan-3-carbonsäureamide und verzweigte Alkancarbonsäureamide.Preferred substances with a physiological cooling effect are menthyl esters, menthone acetals, menthane-3-carboxamides and branched alkanecarboxamides.
Desweiteren bevorzugte Stoffe mit einer physiologischen Kühlwirkung sind Menthyloxamat, Menthyl-N-methyloxamat, Menthyl-N,N-dimethyloxamat, Menthyl-N-ethyloxamat, Menthyl-N,N-diethyloxamat, Menthyl-N-propyloxamat, Menthyl-N,N-dipropyloxamat, Menthyl-N-isopropyloxamat, Menthyl-N,N-diisopropyloxamat, Menthyl-N-cyclopropyloxamat, Menthyl-N-butyloxamat, Morpholin-4-yl-oxo-essigsäure-(1R,2S,5R)-2-isopropyl-5-methyl-cyclohexylester, Menthyl-N-(2-methoxyethyl)-oxamat, Menthyl-N-(3-methoxypropyl)-oxamat, Menthyl-N-(2-hydroxyethyl)-oxamat, Menthyl-N-(3-hydroxypropyl)-oxamat.Further preferred substances having a physiological cooling effect are menthyloxamate, menthyl N-methyloxamate, menthyl N, N-dimethyloxamate, menthyl N-ethyloxamate, menthyl N, N-diethyloxamate, menthyl N-propyloxamate, menthyl N, N- dipropyloxamate, menthyl N-isopropyloxamate, menthyl N, N-diisopropyloxamate, menthyl N-cyclopropyloxamate, menthyl N-butyloxamate, morpholin-4-yl-oxo-acetic acid (1R, 2S, 5R) -2-isopropyl 5-methylcyclohexyl ester, menthyl N- (2-methoxyethyl) oxamate, menthyl N- (3-methoxypropyl) oxamate, menthyl N- (2-hydroxyethyl) oxamate, menthyl N- (3-hydroxypropyl ) oxamate.
In erfindungsgemäßen Mischungen sind einer oder mehrere der Aromastoffe ohne physiologische Kühlwirkung ausgewählt sind aus der Gruppe bestehend aus Stoffen, die einen scharfen Geschmack oder eine Wärme- oder Hitzempfindung auf Haut und Schleimhäuten oder ein Prickel-, bzw. Kribbelgefühl im Mund- und Rachenraum hervorrufen, insbesondere Paprikapulver, Chili-Pfeffer-Pulver, Extrakte aus Paprika, Extrakte aus Pfeffer, Extrakte aus Chili-Pfeffer, Extrakte aus Ingwerwurzeln, Extrakte aus Paradieskörnern (Aframomum melegueta), Extrakte aus Parakresse (Jambu-Oleoresin; Spilanthes acmella, bzw. Spilanthes oleracea), Extrakte aus Japanischem Pfeffer (Zanthoxylum piperitum), Extrakte aus Kaempferia galanga, Extrakte aus Alpinia galanga, Extrakte aus Wasserpfeffer (Polygonium hydropiper), Capsaicin, Dihydrocapsaicin, Gingerol, Paradol, Shogaol, Piperin, Saanshool-I, Saanshool-II, Sanshoamid, Spilanthol, Carbonsäure-N-Vanillylamide, insbesonders Nonansäure-N-vanillylamid, 2-Nonensäureamide, insbesonders 2-Nonensäure-N-isobutylamid, 2-Nonensäure-N-4-hydroxy-3-methoxyphenylamid, 2,4-Decadiensäureamide, vorzugsweise 2,4-Decadiensäure-N-isobutylamide, insbesondere Pellitorine gemäß
In Aromakompositionen beträgt die eingesetzte Gesamtmenge der erfindungsgemäßen alkylierten Tetrahydropyrane vorzugsweise 0,5 bis 30 Gew.-%, vorzugsweise 1 bis 20 Gew.-% und besonders bevorzugt 2 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Aromakomposition.In flavor compositions, the total amount of the alkylated tetrahydropyrans used according to the invention is preferably 0.5 to 30% by weight, preferably 1 to 20% by weight and more preferably 2 to 10% by weight, based on the total weight of the aroma composition.
Erfindungsgemäß angegeben wird ferner eine der Ernährung, der Mundhygiene oder dem Genuss dienende Zubereitung oder pharmazeutische oder kosmetische Zubereitung, umfassend (i) ein oder mehrere erfindungsgemäße alkylierte Tetrahydropyrane oder (ii) eine erfindungsgemäße Mischung, wobei der Bestandteil (i) oder, wenn vorhanden, (ii) vorliegt in einer ausreichenden Konzentration
- zum Erreichen einer physiologischen Kühlwirkung auf der Haut und/oder einer Schleimhaut und/oder
- zum Vermitteln, Modifizieren oder Verstärken eines Frischegefühls in Mund, Rachen und/oder den Atemwegen.
- for achieving a physiological cooling effect on the skin and / or a mucous membrane and / or
- to mediate, modify or enhance a sense of freshness in the mouth, throat and / or respiratory tract.
Die erfindungsgemäßen alkylierten Tetrahydropyrane liegen (vorzugsweise als Bestandteil einer Aromakompositionen in den oben angegebenen Mengenbereichen), je nach Zubereitungsart, allgemein in solchen Zubereitungen vorzugsweise in einem Gesamtanteil von 10 ppm bis 2 Gew.-% vor. Bevorzugt ist ein Gehalt von 25 ppm bis 1 Gew.-%; besonders bevorzugt ein Gehalt von 50 ppm bis 0,5 Gew.-%, am meisten bevorzugt ein Gehalt von 100 ppm - 0,25 Gew.-%, jeweils bezogen auf die gesamte Zubereitung. Zu bestimmten besonders bevorzugten Zubereitungen, insbesondere Mundhygieneprodukten, werden nachfolgend weitere bevorzugte Gehalte genannt.The alkylated tetrahydropyrans according to the invention are present (preferably as constituents of an aroma composition in the abovementioned quantitative ranges), depending on the preparation, generally in such preparations, preferably in a total proportion of from 10 ppm to 2% by weight. Preferred is a content of 25 ppm to 1 wt .-%; Particularly preferred is a content of 50 ppm to 0.5 wt .-%, most preferably a content of 100 ppm - 0.25 wt .-%, each based on the total preparation. For certain particularly preferred preparations, in particular oral hygiene products, further preferred contents are mentioned below.
Die die erfindungsgemäßen Verbindungen enthaltenden Aroma- oder Geschmacksstoffkompositionen können in reiner Form, als Lösungen oder auch in besonders zubereiteter Form verwendet und in gebrauchsfertige Produkte eingearbeitet werden.The flavor or flavor compositions containing the compounds of the invention can be used in pure form, as solutions or in specially prepared form and incorporated into ready-to-use products.
Als Lösungsmittel eignen sich z.B. Ethylalkohol, 1,2-Propylenglycol, Glycerin, Triacetin, Benzylakohol und fette Öle wie z.B. Kokosöl oder Sonnenblumenöl.Suitable solvents are e.g. Ethyl alcohol, 1,2-propylene glycol, glycerin, triacetin, benzyl alcohol and fatty oils such as e.g. Coconut oil or sunflower oil.
Die die erfindungsgemäßen Verbindungen enthaltenden Zubereitungen können auch Zusatz- und Hilfsstoffe,insbesondere Konservierungsstoffe, Farbstoffe, Antioxidantien, Fließmittel, Verdickungsmittel, etc. enthalten.The preparations containing the compounds according to the invention may also contain additives and auxiliaries, in particular preservatives, dyes, antioxidants, flow agents, thickeners, etc.
Die erfindungsgemäßen Verbindungen können an einen Träger gebunden, sprühgetrocknet oder auch verkapselt vorliegen. In der gebundenen Form können erfindungsgemäßen Verbindungen an oder in einen Träger gebunden sein, z.B. Kochsalz, Zucker, Stärken oder Zuckerschmelzen. Die sprühgetrocknete Form wird aus den flüssigen Kompositionen hergestellt, indem man eine Emulsion unter Zugabe von bestimmten Mengen eines Trägerstoffs, vorzugsweise Biopolymere wie Stärke, modizierte Stärken, Maltodextrin und Gummi Arabicum, herstellt. Diese Emulsion wird in Sprühtrocknern durch Feinstverteilung bei gleichzeitiger Temperaturanwendung getrocknet. Es resultiert ein Pulver mit der gewünschten Beladung an flüssiger Komposition. Die verkapselte Form wird ebenfalls aus den flüssigen Kompositionen durch Zugabe eines Trägerstoffs hergestellt. Es gibt verschiedenen Technologien, mit denen Kapseln hergestellt werden können. Die gängigsten sind die Extrusion, die Sprühgranulation und die Coazervation. Die Partikelgrößen reichen üblicherweise von 10 µm bis 5 mm. Die gängigsten Kapselmaterialien sind verschiedene Stärken, Maltodextrin und Gelatine. In diesen Kapseln sind die flüssigen oder festen Aroma- oder Geschmacksstoffkompositionen eingeschlossen und können durch verschiedene Mechanismen wie Wärmeanwendung, pH-Verschiebung oder Kaudruck freigesetzt werden.The compounds of the invention may be bound to a carrier, spray-dried or encapsulated. In the bonded form, compounds of the invention may be bound to or in a carrier, e.g. Table salt, sugar, starches or sugar melts. The spray-dried form is prepared from the liquid compositions by preparing an emulsion with the addition of certain amounts of a carrier, preferably biopolymers such as starch, modified starches, maltodextrin and gum arabic. This emulsion is dried in spray dryers by very fine distribution with simultaneous temperature application. The result is a powder with the desired loading of liquid composition. The encapsulated form is also prepared from the liquid compositions by adding a carrier. There are several technologies that can be used to make capsules. The most common are extrusion, spray granulation and coacervation. The particle sizes usually range from 10 μm to 5 mm. The most common capsule materials are various starches, maltodextrin and gelatin. These capsules contain the liquid or solid flavor or flavor compositions and can be released by various mechanisms such as heat application, pH shift or chewing pressure.
Die die erfindungsgemäßen Verbindungen enthaltenden Zubereitungen können vorteilhaft vor allem in Mundhygieneprodukten, wie Zahnpasten und Mundwässern, Kaugummis, Nahrungsmitteln, wie Süßwaren und Lutschbonbons, Genußmitteln wie Tabak und pharmazeutischen Präparaten und Nasensprays eingesetzt werden.The formulations containing the compounds according to the invention can advantageously be used above all in oral hygiene products such as toothpastes and mouthwashes, chewing gums, foods such as confectionery and lozenges, stimulants such as tobacco and pharmaceutical preparations and nasal sprays.
Der Gesamtgehalt einer Aromakomposition enthaltend eine oder mehrere erfindungsgemäße Verbindungen beträgt in gebrauchsfertigen Mundwässern vorzugsweise 0,01 bis 1 Gew.%, bevorzugt 0,05 bis 0,5 Gew.-%, besonders bevorzugt ist ein Gehalt von 0,1 bis 0,3 Gew.-%, jeweils bezogen auf das gesamte Mundwasser.The total content of an aroma composition containing one or more compounds according to the invention in ready-to-use mouthwashes is preferably from 0.01 to 1% by weight, preferably from 0.05 to 0.5% by weight, more preferably from 0.1 to 0.3 Wt .-%, in each case based on the total mouthwash.
In Mundwasserkonzentraten beträgt der Gesamtgehalt der Aromakomposition enthaltend eine oder mehrere erfindungsgemäße Verbindungen vorzugsweise 0,1 bis 15 Gew.-%, bevorzugt ist ein Gehalt von 0,5 bis 8 Gew.-%, besonders bevorzugt 1 bis 5 Gew.-%, jeweils bezogen auf das gesamte Mundwasserkonzentrat.In mouthwash concentrates, the total content of the aroma composition containing one or more compounds of the invention is preferably 0.1 to 15 wt .-%, preferably, a content of 0.5 to 8 wt .-%, particularly preferably 1 to 5 wt .-%, respectively based on the entire mouthwash concentrate.
In Zahnpasten beträgt der Gesamtgehalt der Aromakomposition enthaltend eine oder mehrere erfindungsgemäße Verbindungen vorzugsweise 0,1 bis 5 Gew.-%, bevorzugt 0,5 bis 2 Gew.-%, besonders bevorzugt 0,8 bis 1,5 Gew.-%, jeweils bezogen auf die gesamte Zahnpasta.In toothpastes, the total content of the aroma composition containing one or more compounds according to the invention is preferably 0.1 to 5% by weight, preferably 0.5 to 2% by weight, particularly preferably 0.8 to 1.5% by weight, in each case based on the total toothpaste.
In Kaugummis beträgt der Gesamtgehalt der Aromakomposition enthaltend eine oder mehrere erfindungsgemäße Verbindungen vorzugsweise 0,1 bis 5 Gew.-%, bevorzugt 0,5 bis 3 Gew.-%, besonders bevorzugt 0,8 bis 2,5 Gew.-%, jeweils bezogen auf das gesamte Kaugummi.In chewing gums, the total content of the aroma composition containing one or more compounds according to the invention is preferably from 0.1 to 5% by weight, preferably from 0.5 to 3% by weight, particularly preferably from 0.8 to 2.5% by weight, in each case based on the total chewing gum.
In Lutschbonbons (Hartkaramellen) beträgt der Gesamtgehalt der Aromakomposition enthaltend eine oder mehrere erfindungsgemäße Verbindungen vorzugsweise 0,01 bis 2 Gew.-%, bevorzugt 0,05 bis 1 Gew.-%, besonders bevorzugt 0,1 bis 0,5 Gew.-%, jeweils bezogen auf das gesamte Lutschbonbon.In hard candies, the total content of the aroma composition containing one or more compounds according to the invention is preferably from 0.01 to 2% by weight, preferably from 0.05 to 1% by weight, more preferably from 0.1 to 0.5% by weight. %, in each case based on the whole lollipop.
- (i) eine der Ernährung oder dem Genuss dienende Zubereitung ausgewählt aus Backwaren, Süßwaren, alkoholische oder nicht-alkoholische Getränke, Instantgetränke, Fleischprodukte, Eier oder Eiprodukte , Getreideprodukte, Milchprodukte, Fruchtzubereitungen, Gemüsezubereitungen, Knabberartikel, Produkte auf Fett- und Ölbasis oder Emulsionen derselben, sonstige Fertiggerichte und Suppen, Gewürze, Würzmischungen, Aufstreuwürzungen, Halbfertigwaren, Nahrungsergänzungsmittel; oder(i) a nutrition or pleasure preparation selected from bakery products, confectionery, alcoholic or non-alcoholic beverages, instant drinks, meat products, eggs or egg products, cereals, dairy products, fruit preparations, vegetable preparations, snack foods, fat and oil based products or emulsions the same, other prepared meals and soups, spices, seasoning mixes, sprinkling seasonings, semi-prepared goods, food supplements; or
- (ii) eine der Mundhygiene dienende Zubereitung, vorzugsweise auf Basis eines Zahnpflegemittels, und ausgewählt aus der Gruppe bestehend aus: Zahnpasta, Zahncreme, Zahngel, Zahnpulver, Zahnputzflüssigkeit, Zahnputzschaum, Mundwasser, Zahncreme und Mundwasser als 2-in-1 Produkt, Lutschbonbon, Mundspray, Zahnseide und Zahnpflegekaugummi; oder(ii) an oral hygiene preparation, preferably based on a dentifrice, and selected from the group consisting of: toothpaste, toothpaste, dental gel, tooth powder, dentifrice, toothpaste, mouthwash, toothpaste and mouthwash as a 2-in-1 product, lollipop, Oral spray, dental floss and dental care gum; or
- (iii) eine pharmazeutische Zubereitung, wobei die Zubereitung vorzugsweise eine orale pharmazeutische Zubereitung oder eine nasal zu applizierende Zubereitung ist, vorzugsweise in Form von Kapseln, Tabletten, Dragees, Granulaten, Pellets, Feststoffmischungen, Dispersionen in flüssigen Phasen, als Emulsionen, als Pulver, als Lösungen, als Pasten oder als andere schluck- oder kaubare Zubereitung; oder(iii) a pharmaceutical preparation, wherein the preparation is preferably an oral pharmaceutical preparation or a preparation to be applied nasally, preferably in the form of capsules, tablets, dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powder, as solutions, as pastes or as another swallowable or chewable preparation; or
- (iv) eine kosmetische Zubereitung, ausgewählt aus der Gruppe bestehend aus: Seife, Syndet, flüssiges Wasch-, Dusch-, oder Badepräparat, Emulsion, Salbe, Paste, Gel, Öl, Toner, Balsam, Serum, Puder, Eau de Toilette, Toilette, Eau de Cologne, Parfum, Wachs, Stift, Roll-On, (Pump-)Spray, Aerosol (schäumend, nicht schäumend oder nachschäumend), Fußpflegemittel, Bartreinigungs- oder -pflegemittel, Insekten abwehrendes Mittel, Sonnenschutzmittel, Aftersun-Präparat, Rasiermittel, After-Shave, Haarentfernungsmittel, Haarpflegemittel, Conditioner, Haarkur, Haarwasser, Haarspülung, Frisiercreme, Pomade, Dauerwell- und Fixierungsmittel, Haarglättungsmittel, Haarfestiger, Styling-Hilfe, Blondiermittel, Haaraufheller, Haarconditioner, Haarmousse, Haartönung, Nagelpflegemittel, Deodorant, Antitranspirant, Mundwasser, Munddusche, Make-Up, Make-Up-Entferner, Augenpflege, Lippenkosmetika, Lippenpflegemittel, dekorative Kosmetik, Badeartikel und Maske.(iv) a cosmetic preparation selected from the group consisting of: soap, syndet, liquid washing, showering or bathing preparation, emulsion, ointment, paste, gel, oil, toner, balm, serum, powder, eau de toilette, Toilet, cologne, perfume, wax, stick, roll-on, (pump) spray, aerosol (foaming, non-foaming or post-foaming), foot care, beard care or conditioner, insect repellent, sunscreen, aftersun preparation, Shaving, after-shave, depilatory, hair care, conditioner, hair conditioner, hair conditioner, hair conditioner, styling cream, pomade, perming and fixing agent, hair straightener, hair setting, styling aid, bleach, hair lightener, hair conditioner, hair mousse, hair tint, nail care, deodorant, antiperspirant , Mouthwash, irrigator, make-up, make-up remover, eye care, lip cosmetics, lip balm, decorative cosmetics, bath products and mask.
Der Mundhygiene dienende Zubereitungen, insbesondere Zahnpasten, die mit den die erfindungsgemäßen Verbindungen enthaltenden Kompositionen aromatisiert werden, bestehen im allgemeinen aus einem abrasiven System (Schleif- oder Poliermittel), wie z.B. Kieselsäuren, Calciumcarbonaten, Calciumphosphaten, Alumiuniumoxiden und/oder Hydroxylapatiten, aus oberflächenaktiven Substanzen, wie z.B. Natriumlaurylsulfat, Natriumlaurylsarcosinat und/oder Cocamidopropylbetain, aus Feuchthaltemitteln, wie z.B. Glycerin und/oder Sorbit, aus Verdickungsmitteln, wie z.B. Carboxymethylcellulose, Polyethylenglycolen, Carrageenanen und/oder Laponiten®, aus Süßstoffen, wie z.B. Saccharin, aus Kühlwirkstoffen, aus Stabilisatoren und aus aktiven Wirkstoffen, wie z.B. Natriumfluorid, Natriummonofluorphosphat, Zinndifluorid, quartären Ammoniumfluoriden, Zinkcitrat, Zinksulfat, Zinnpyrophosphat, Zinndichlorid, Mischungen verschiedener Pyrophosphate, Triclosan, Cetylpyridiniumchlorid, Aluminiumlactat, Kaliumcitrat, Kaliumnitrat, Kaliumchlorid, Strontiumchlorid, Wasserstoffperoxid, und/oder Natriumbicarbonat.Oral hygiene preparations, in particular toothpastes flavored with compositions containing the compounds of the invention, generally consist of an abrasive system (abrasives or abrasives), such as silicic acids, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites, of surfactants , such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or Cocamidopropylbetain, from humectants, such as glycerol and / or sorbitol, thickeners, such as carboxymethylcellulose, polyethylene glycols, carrageenans and / or Laponites ® , from sweeteners, such as saccharin, cooling agents, stabilizers and active ingredients such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, Potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, and / or sodium bicarbonate.
Kaugummis, die mit den die erfindungsgemäßen Verbindungen enthaltenden Kompositionen aromatisiert werden, umfassen im allgemeinen eine Kaugummibase, d.h. eine beim Kauen plastisch werdende Kaumasse, Zucker verschiedener Arten, Zuckeraustauschstoffe, andere süß schmeckende Stoffe, Zuckeralkohole (insbesondere Sorbitol, Xylitol, Mannitol), Kühlwirkstoffe, Geschmackskorrigenzien für unangenehme Geschmackseindrücke, andere Geschmacksmodulatoren für weitere, in der Regel nicht unangenehme Geschmackseindrücke, geschmacksmodulierende Stoffe (z.B. Inositolphosphat, Nucleotide wie Guanosinmonophosphat, Adenosinmonophosphat oder andere Stoffe wie Natriumglutamat oder 2-Phenoxypropionsäure), Feuchthaltemittel, Verdicker, Emulgatoren und Stabilisatoren.Chewing gums flavored with the compositions containing the compounds of the invention generally comprise a chewing gum base, ie chewing gum that becomes plastic upon chewing, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols (especially sorbitol, xylitol, mannitol), cooling agents, flavoring agents for unpleasant taste impressions, other flavor modulators for other, usually not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers and stabilizers.
Im Stand der Technik sind zahlreiche unterschiedliche Kaugummibasen bekannt, wobei zwischen sogenannten "chewing gum" - oder um "bubble gum" - Basen zu unterscheiden ist, wobei letztere weicher sind, damit sich damit auch Kaugummiblasen bilden lassen. Gängige Kaugummibasen umfassen neben traditionell eingesetzten natürlichen Harzen oder dem Naturlatex Chicle heute zumeist Elastomere wie Polyvinylacetate (PVA), Polyethylene, (nieder- oder mittelmolekulare) Polyisobutene (PIB), Polybutadiene, Isobuten-Isopren Copolymere (Butyl Rubber), Polyvinylethylether (PVE), Polyvinylbutylether, Copolymere von Vinylestern und Vinylethern, Styrol-Butadien-Copolymere (Styrol-Butadien-Rubber, SBR) oder Vinyl-Elastomere, z.B. auf Basis Vinylacetat/Vinyllaurat, Vinylacetat/Vinylstaerat oder Ethylen/Vinylacetat, sowie Mischungen der genannten Elastomere, wie beispielsweise in
Bei der Anwendung von Fertigprodukten, die Kompositionen mit den erfindungsgemäßen Verbindungen enthalten, zeigt es sich, dass die erfindungsgemäßen Verbindungen, bzw. die die erfindungsgemäßen Verbindungen enthaltenden Kompositionen sich besonders dafür eignen, die Atemluft zu erfrischen und schlechten Mundgeruch zu neutralisieren, bzw. zu reduzieren.In the case of the use of finished products which comprise compositions with the compounds according to the invention, it is found that the compounds according to the invention or the compositions containing the compounds according to the invention are particularly particular are suitable for refreshing the respiratory air and neutralizing or reducing bad halitosis.
Die Verwendung der erfindungsgemäßen Verbindungen, bzw. der die erfindungsgemäßen Verbindungen enthaltenden Mischungen in Mundpflegeprodukten (Mundhygieneprodukten), wie z. B. Mundwässern und Zahnpasten, und Kaugummis führt dazu, dass unangenehme, vor allem bittere oder metallische Geschmackseindrücke teilweise maskiert oder neutralisiert werden, die z.B. durch Stoffe wie Triclosan, Zinkcitrat, -sulfat, Poly- und Pyrophosphaten, Bicarbonate, Strontium- und Kaliumsalze, Zinnpyrophosphat, - chlorid, Aluminiumlactat, Wasserstoffperoxid, Fluoride, Vitamine, Cetylpyridiniumchlorid sowie von Emulgatoren, wie z.B. besonders Natriumlaurylsulfat, Natriumlaurylsarkosinat und Cocamidopropylbetain, und Süßstoffen, wie z.B. Aspartam, Saccharin, Acesulfam-K, Sorbit; Xylit, Cyclamate (z.B. Natriumcyclamat), Sucralose, Alitam, Neotam, Thaumatin, Neohesperidin Dihydrochalcon, Maltit, Lactit oder Kaugummi-Massen hervorgerufen werden.The use of the compounds according to the invention, or of the compounds according to the invention containing mixtures in oral care products (oral hygiene products), such as. As mouthwashes and toothpastes, and chewing gum causes unpleasant, especially bitter or metallic taste impressions are partially masked or neutralized, the e.g. by substances such as triclosan, zinc citrate, sulphate, poly- and pyrophosphates, bicarbonates, strontium and potassium salts, tin pyrophosphate, chloride, aluminum lactate, hydrogen peroxide, fluorides, vitamins, cetylpyridinium chloride and emulsifiers, e.g. especially sodium lauryl sulfate, sodium lauryl sarcosinate and cocamidopropyl betaine, and sweeteners such as e.g. Aspartame, saccharin, acesulfame-K, sorbitol; Xylitol, cyclamates (e.g., sodium cyclamate), sucralose, alitame, neotame, thaumatin, neohesperidin dihydrochalcone, maltitol, lactitol, or chewing gum masses.
Als weitere positive Eigenschaft der erfindungsgemäßen Verbindungen ist ihre Stabilität in Zahnpasten auf Kreide- oder Bicarbonatbasis hervorzuheben, die wegen ihres alkalischen pH-Wertes schwierig zu aromatisieren sind.Another positive feature of the compounds according to the invention is their stability in chalk or bicarbonate based toothpastes, which are difficult to flavor because of their alkaline pH.
Die erfindungsgemäßen Verbindungen, bzw. die die erfindungsgemäßen Verbindungen enthaltenden Kompositionen eignen sich jedoch auch für den Einsatz in pharmazeutischen Präparaten, wie z. B. Nasentropfen und -sprays oder Einreibepräparaten. Insbesondere eignen sich die die erfindungsgemäßen Verbindungen enthaltenden Kompositionen für die Maskierung des bitteren Geschmacks von Medikamenten.However, the compounds according to the invention or the compositions containing the compounds according to the invention are also suitable for use in pharmaceutical preparations, such as. As nasal drops and sprays or Einreibepräparaten. In particular, the compositions containing the compounds according to the invention are suitable for masking the bitter taste of medicaments.
Weitere Aspekte der vorliegenden Erfindung ergeben sich aus den nachfolgenden Beispielen sowie der beigefügten Patentansprüchen. Sofern nicht anders angegeben, beziehen sich alle Angaben auf das Gewicht.Further aspects of the present invention will become apparent from the following examples and the appended claims. Unless otherwise indicated, all data are by weight.
In manchen Beispielen wurde eine Pellitorin-Lösung (im Folgenden als "Pellitorin Lösung PLM" bezeichnet) eingesetzt bestehend aus 10% Pellitorin (umfassend 4,9% 2E,4Z-Decadiensäure-N-isobutylamid und 94,3% 2E,4E-Decadiensäure-N-isobutylamid), 45% Propylenglycol und 45% natürliches Pfefferminzöl (Mentha arvensis).In some examples, a pellitorin solution (hereinafter referred to as "pellitorin solution PLM") consisting of 10% pellitorin (comprising 4.9% 2E, 4Z-decadienoic acid N-isobutylamide and 94.3% 2E, 4E-decadienoic acid N-isobutylamide), 45% propylene glycol and 45% natural peppermint oil ( Mentha arvensis ).
Es wurden zwei Zahnpastaproben [Zahnpastaformulierung I aus Beispiel 2.15 ("Silica Opaque"), Aroma aus Beispiel 2.1 ("Pfefferminztyp")] gegeneinander verglichen. Die Probanden waren aufgefordert sich eine Minute lang die Zähne zu putzen und anschliessend die Proben sensorisch zu bewerten. Abgefragt wurden die unten im Netzdiagramm aufgeführten Deskriptoren (Skala von 0 (= entspricht nicht dem Deskriptor) bis 8 (entspricht sehr stark dem Deskriptor)).Two toothpaste samples [toothpaste formulation I from Example 2.15 ("Silica Opaque"), flavor from Example 2.1 ("peppermint type")] were compared with one another. The subjects were asked to brush their teeth for one minute and then to evaluate the samples by sensor. The descriptors listed below in the net diagram were queried (scale from 0 (= does not correspond to the descriptor) to 8 (corresponds very much to the descriptor)).
Eine Probe enthielt das Aroma "Pfefferminztyp" ohne erfindungsgemäße Verbindungen (Dosierung 0,9 %; ausgefüllter Bereich der
Die erfindungsgemäßen Verbindungen verändern demnach nicht das Geschmacksprofil des Aromas; vielmehr verstärken sie dessen Geschmackseindruck in gewünschter Art und Weise. Der Eindruck von Frische und Fülle wird verstärkt und die Gesamtwirkung des Aromas entfaltet sich besser. Insbesondere in der Anfangsphase des Bürstens (beim Aufschäumen der Paste) wird der Geschmackseindruck deutlich verstärkt (Deskriptoren "Freshness during" (Frische während des Putzens) und "Impact" (Gesamtgeschmackseindruck 10 Sekunden nach dem Putzen). Von 13 Probanden bevorzugten 9 das Muster, welches die erfindungsgemäßen Verbindungen enthielt (vgl.
In einem 2L-Doppelmantelreaktor mit Thermometer und Tropftrichter wurden 46 g Wasser vorlegt und 346 g Phosphorsäure (85%ig) zugegeben (also auf 75 %ige Konzentration verdünnt) und anschließend auf 0°C gekühlt.
116,2 g Propionaldehyd mit 308,5 g Linalool wurden gemischt und unter starkem Rühren in ca. 1h bis zu einer maximalen Innentemperatur von 5°C zugetropft. Den Ansatz wurde nach beendeter Zugabe weitere 4 h bei 0°C bis 5°C nachgerührt, dann auf Raumtemperatur (ca. 20°C) erwärmt. Anschließend wurde zur vollständigen Umsetzung für etwas 20 Minuten auf 70 °C aufgeheizt. Bei 65 - 70°C wurde die Phasen getrennt. Die organische Phase wurde zweimal mit jeweils 100 g Wasser gewaschen und anschließend der Rohansatz über eine 30 cm Füllkörperkolonne destilliert. Es wurden 251 g Produkt mit einerm Gehalt von 84% an 6-Ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran erhalten (54% Ausbeute der Theorie).In a 2L jacketed reactor with thermometer and dropping funnel 46 g of water were initially charged and 346 g of phosphoric acid (85%) was added (ie diluted to 75% concentration) and then cooled to 0 ° C.
116.2 g of propionaldehyde with 308.5 g of linalool were mixed and added dropwise with vigorous stirring in about 1 h up to a maximum internal temperature of 5 ° C. After the addition had ended, the mixture was stirred at 0 ° C. to 5 ° C. for a further 4 h, then warmed to room temperature (about 20 ° C.). It was then heated to 70 ° C for complete reaction for about 20 minutes. At 65-70 ° C, the phases were separated. The organic phase was washed twice with 100 g of water and then the crude batch was distilled over a 30 cm packed column. There were obtained 251 g of product with a content of 84% of 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran (54% yield of theory).
Die Hydrierung wurde in einem Hydrierautoklaven durchgeführt. Es wurden 202 g 6-Ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran (aus der 1. Stufe) mit 8 g Pd/Aktivkohle (Pd-Gehalt: 5%) in den Autoklaven gefüllt und bei 30 bar Wasserstoffdruck hydriert. Die Reaktion verlief exotherm von 20°C bis etwa 50°C, danach wurde auf 90°C geheizt. Die H2-Aufnahme war nach 35 min beendet. Es wurden 107% H2 derTheorie aufgenommen. Der Katalysator wurde abfiltriert und dieser anschließend mit Ethanol nachgespült. Das so erhaltene Material wurde anschließend über 120 cm Kolonne destilliert. Es wurden 131 g 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran (Reinheit > 97 %) erhalten (73% Ausbeute der Theorie).The hydrogenation was carried out in a hydrogenation autoclave. 202 g of 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran (from the 1st stage) were charged to the autoclave with 8 g of Pd / activated carbon (Pd content: 5%) and hydrogenated at 30 bar hydrogen pressure , The reaction was exothermic from 20 ° C to about 50 ° C, then heated to 90 ° C. H 2 uptake was complete after 35 min. 107% H 2 of the theory was recorded. The catalyst was filtered off and then rinsed with ethanol. The material thus obtained was then distilled over 120 cm column. There were obtained 131 g of 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran (purity> 97%) (73% yield of theory).
1H-NMR (Mischung der Isomeren, 400 MHz, CDCl3): δ = 0.92 (t, J = 7.4 Hz, 3 H), 1.18-1.31 (m, 2 H), 1.19 (s, 0.5 × 3 H), 1.28 (s, 0.5 × 3 H), 1.45-1.95 (m, 6 H), 1.62 (dd, J = 0.9 Hz,J=1.5Hz,0.5×3H), 1.70 (dd, J = 1.0 Hz, J = 1.4 Hz, 0.5 × 3 H), 3.45 (ddd, J = 2.6 Hz, J=8.7Hz, J= 10.2 Hz, 0.5 × 1 H), 3.53 (ddd, J = 2.6 Hz, J = 8.2 Hz, J = 9.7 Hz, 0.5 × 1 H), 4.68-4.76 (m, 1 H), 4.89-5.25 (m, 1 H), 5.79 (ddd, J = 1.0 Hz, J = 11.1 Hz, J = 17.8 Hz, 1 H), 5.91 (dd, J = 10.9 Hz, J = 17.4 Hz, 1 H) ppm.
13C-NMR (Mischung der Isomeren, 100 MHz, CDCl3): δ = 10.18 (CH3), 10.33 (CH3), 20.26 (CH3), 20.39 (CH3), 21.03 (CH3), 27.28 (CH2), 27.44 (CH2), 27.60 (CH2), 27.96 (CH2), 27.99 (CH2), 31.55 (CH3), 35.52 (CH2), 35.92 (CH2), 50.87 (CH), 50.96 (CH), 74.38 (C), 74.69 (CH), 76.04 (C), 76.17 (CH), 111.04 (CH2), 112.17 (CH2), 112.21 (CH2), 115.34 (CH2), 144.42 (CH), 147.77 (CH), 148.69 (C) ppm.
MS: m/z (%) = 194 (1) [M+], 136 (10), 121 (19), 107 (14), 93 (32), 81 (11), 68 (100), 53 (8). 1 H-NMR (mixture of isomers, 400 MHz, CDCl 3 ): δ = 0.92 (t, J = 7.4 Hz, 3 H), 1.18-1.31 (m, 2 H), 1.19 (s, 0.5 × 3 H) , 1.28 (s, 0.5 × 3 H), 1.45-1.95 (m, 6H), 1.62 (dd, J = 0.9 Hz, J = 1.5Hz, 0.5 × 3H), 1.70 (dd, J = 1.0 Hz, J = 1.4 Hz, 0.5 × 3 H), 3.45 (ddd, J = 2.6 Hz, J = 8.7 Hz, J = 10.2 Hz, 0.5 × 1 H), 3.53 (ddd, J = 2.6 Hz, J = 8.2 Hz, J = 9.7 Hz, 0.5 × 1 H), 4.68-4.76 (m, 1H), 4.89-5.25 (m, 1H), 5.79 (ddd, J = 1.0 Hz, J = 11.1 Hz, J = 17.8 Hz, 1 H), 5.91 (dd, J = 10.9 Hz, J = 17.4 Hz, 1 H) ppm.
13 C-NMR (mixture of isomers, 100 MHz, CDCl 3 ): δ = 10.18 (CH 3 ), 10.33 (CH 3 ), 20.26 (CH 3 ), 20.39 (CH 3 ), 21.03 (CH 3 ), 27.28 ( CH 2 ), 27.44 (CH 2 ), 27.60 (CH 2 ), 27.96 (CH 2 ), 27.99 (CH 2 ), 31.55 (CH 3 ), 35.52 (CH 2 ), 35.92 (CH 2 ), 50.87 (CH) , 50.96 (CH), 74.38 (C), 74.69 (CH), 76.04 (C), 76.17 (CH), 111.04 (CH 2 ), 112.17 (CH 2 ), 112.21 (CH 2 ), 115.34 (CH 2 ), 144.42 (CH), 147.77 (CH), 148.69 (C) ppm.
MS: m / z (%) = 194 (1) [M + ], 136 (10), 121 (19), 107 (14), 93 (32), 81 (11), 68 (100), 53 ( 8th).
1H-NMR (Mischung der Isomeren, 400 MHz, CDCl3): δ = 0.74-0.96 (m, 12 H), 1.09 (s, 0.5 × 3 H), 1.10 (s, 0.5 × 3 H), 1.10-1.72 (m, 8 H), 1.81-1.93 (m, 2 H), 3.22 (ddd, J = 1.0 Hz, J = 2.7 Hz, J = 8.4 Hz, 0.5 ×1 H), 3.33 (ddd, J = 2.8 Hz, J = 8.2 Hz, J = 10.1 Hz, 0.5 ×1 H) ppm.
13C-NMR (Mischung der Isomeren, 100 MHz, CDCl3): δ = 7.38 (CH3), 7.72 (CH3), 9.59 (CH3), 9.87 (CH3), 15.86 (CH3), 15.88 (CH3), 18.07 (CH2), 18.32 (CH2), 19.39 (CH3), 21.33 (CH3), 25.66 (CH2), 25.78 (CH2), 25.84 (CH2), 26.86 (CH), 26.87 (CH), 27.66 (CH3), 34.89 (CH2), 36.19 (CH2), 37.17 (CH2), 44.70 (CH), 45.13 (CH), 72.50 (C), 72.51 (C), 72.83 (CH), 73.03 (CH) ppm.
MS: m/z (%) = 198 (1) [M+], 169 (66), 151 (79), 111 (25), 109 (21), 95 (48), 83 (18), 70 (100), 55 (57). 1 H-NMR (mixture of isomers, 400 MHz, CDCl 3 ): δ = 0.74-0.96 (m, 12 H), 1.09 (s, 0.5 × 3 H), 1.10 (s, 0.5 × 3 H), 1.10- 1.72 (m, 8H), 1.81-1.93 (m, 2H), 3.22 (ddd, J = 1.0 Hz, J = 2.7 Hz, J = 8.4 Hz, 0.5 × 1 H), 3.33 (ddd, J = 2.8 Hz, J = 8.2 Hz, J = 10.1 Hz, 0.5 × 1 H) ppm.
13 C-NMR (mixture of isomers, 100 MHz, CDCl 3 ): δ = 7.38 (CH 3 ), 7.72 (CH 3 ), 9.59 (CH 3 ), 9.87 (CH 3 ), 15.86 (CH 3 ), 15.88 ( CH 3 ), 18.07 (CH 2 ), 18.32 (CH 2 ), 19.39 (CH 3 ), 21.33 (CH 3 ), 25.66 (CH 2 ), 25.78 (CH 2 ), 25.84 (CH 2 ), 26.86 (CH) , 26.87 (CH), 27.66 (CH 3 ), 34.89 (CH 2 ), 36.19 (CH 2 ), 37.17 (CH 2 ), 44.70 (CH), 45.13 (CH), 72.50 (C), 72.51 (C), 72.83 (CH), 73.03 (CH) ppm.
MS: m / z (%) = 198 (1) [M + ], 169 (66), 151 (79), 111 (25), 109 (21), 95 (48), 83 (18), 70 ( 100), 55 (57).
In einem 2L-Dreihalskolben wurden 42 g Acetaldehyd in 600 mL Diethylether vorgelegt und auf 0°C abgekühlt. Anschließend wurden 140 g einer 48%igen Lösung von Bortrifluorid-Diethyletherat zugegeben und 10 Minuten bei 0°C gerührt. Zur Reaktionslösung wurden bei 0°C 124 g 2,6-Dimethyl-hept-5-en-2-ol in 100 mL Diethylether gelöst zugetropft. Nach vollendeter Zugabe wurde noch eine Stunde bei 0°C nachgerührt und anschließend auf Raumtemperatur erwärmt. Nachdem die Reaktionslösung 12 Stunden bei Raumtemperatur gerührt worden war, wurde mit gesättigter Ammoniumchloridlösung (500 mL) gequencht und nach Aufarbeitung das erhaltene Rohprodukt über eine 30 cm Füllkörperkolonne destilliert. Es wurden 82 g 2,2,6-Trimethyl-5-isopropenyltetrahydropyran in 98%iger Reinheit erhalten. (55% Ausbeute der Theorie).
Das 2,2,6-Trimethyl-5-isopropyltetrahydropyran wurde durch Hydrierung (analog der 2. Stufe aus Beispiel 1.1) von 2,2,6-Trimethyl-5-isopropenyltetrahydropyran und anschließender Destillation in 85%iger Ausbeute erhalten.42 g of acetaldehyde in 600 ml of diethyl ether were placed in a 2L three-necked flask and cooled to 0 ° C. Subsequently, 140 g of a 48% solution of boron trifluoride diethyl etherate was added and stirred at 0 ° C for 10 minutes. 124 g of 2,6-dimethyl-hept-5-en-2-ol dissolved in 100 ml of diethyl ether were added dropwise at 0 ° C. to the reaction solution. After completion of the addition, the mixture was stirred for a further hour at 0 ° C and then warmed to room temperature. After the reaction solution had been stirred for 12 hours at room temperature, it was quenched with saturated ammonium chloride solution (500 ml) and, after working up, the crude product obtained was distilled through a 30 cm packed column. There were obtained 82 g of 2,2,6-trimethyl-5-isopropenyltetrahydropyran in 98% purity. (55% yield of theory).
The 2,2,6-trimethyl-5-isopropyltetrahydropyran was obtained by hydrogenation (analogously to the 2nd stage from Example 1.1) of 2,2,6-trimethyl-5-isopropenyltetrahydropyran and subsequent distillation in 85% yield.
1H-NMR (400 MHz, CDCl3): δ = 0.79 (d, J = 6.9 Hz, 3 H), 0.91 (d, J = 7.0 Hz, 3 H), 1.00-1.10 (m, 1 H), 1.11-1.60 (m, 4 H), 1.14 (d, J=6.1 Hz, 3 H), 1.18 (s, 3 H), 1.20 (s, 3 H), 1.87 (dhept., J = 3.2 Hz, J = 6.9 Hz, 1 H), 3.56 (dq, J = 6.1 Hz, J = 10.1 Hz, 1 H) ppm.
13C-NMR (100 MHz, CDCl3): = 15.79 (CH3), 18.44 (CH2), 20.05 (CH3), 21.31 (CH3), 22.08 (CH3), 27.25 (CH), 31.74 (CH3), 36.86 (CH2), 47.59 (CH), 69.15 (CH), 71.36 (C) ppm.
MS: m/z (%) = 170 (1) [M+], 155 (21), 137 (8), 126 (22), 111 (3), 97 (5), 84 (22), 69 (36), 56 (100), 43 (30). 1 H-NMR (400 MHz, CDCl 3 ): δ = 0.79 (d, J = 6.9 Hz, 3 H), 0.91 (d, J = 7.0 Hz, 3 H), 1.00-1.10 (m, 1 H), 1.11-1.60 (m, 4H), 1.14 (d, J = 6.1 Hz, 3H), 1.18 (s, 3H), 1.20 (s, 3H), 1.87 (dhept., J = 3.2 Hz, J = 6.9 Hz, 1 H), 3.56 (dq, J = 6.1 Hz, J = 10.1 Hz, 1 H) ppm.
13 C-NMR (100 MHz, CDCl3): = 15.79 (CH 3), 18:44 (CH2), 20.5 (CH 3), 21:31 (CH 3), 22.8 (CH3), 27.25 (CH), 31.74 ( CH 3 ), 36.86 (CH 2 ), 47.59 (CH), 69.15 (CH), 71.36 (C) ppm.
MS: m / z (%) = 170 (1) [M + ], 155 (21), 137 (8), 126 (22), 111 (3), 97 (5), 84 (22), 69 ( 36), 56 (100), 43 (30).
1H-NMR (400 MHz, CDCl3): δ = 0.77 (d, J = 6.9 Hz, 3 H), 0.78-0.90 (m, 1 H), 0.83 (t, J = 7.48 Hz, 3 H), 0.90 (d, J = 6.9 Hz, 3 H), 1.03-1.13 (m, 1 H), 1.10 (s, 3 H), 1.13 (d, J = 6.12 Hz, 3 H), 1.25-1.48 (m, 4 H), 1.55-1.61 (m, 1 H), 1.79-1.89 (m, 1 H), 3.44 (dq, J = 6.1 Hz, J = 10.0 Hz, 1 H) ppm.
13C-NMR (100 MHz, CDCl3): δ = 7.59 (CH3), 15.83 (CH3), 18.12 (CH2), 20.04 (CH3), 21.31 (CH3), 25.93 (CH2), 27.30 (CH), 27.80 (CH3), 35.90 (CH2), 47.31 (CH), 68.35 (CH), 72.89 (C) ppm.
MS: m/z (%) = 185 (1) [MH+], 169 (1), 155 (79), 137 (100), 111 (6), 97 (43), 81 (24), 70 (72), 55 (59). 1 H-NMR (400 MHz, CDCl 3 ): δ = 0.77 (d, J = 6.9 Hz, 3 H), 0.78-0.90 (m, 1 H), 0.83 (t, J = 7.48 Hz, 3 H), 0.90 (d, J = 6.9Hz, 3H), 1.03-1.13 (m, 1H), 1.10 (s, 3H), 1.13 (d, J = 6.12Hz, 3H), 1.25-1.48 (m, 4H), 1.55-1.61 (m, 1H), 1.79-1.89 (m, 1H), 3.44 (dq, J = 6.1 Hz, J = 10.0 Hz, 1H) ppm.
13 C-NMR (100 MHz, CDCl 3): δ = 7:59 (CH 3), 15.83 (CH3), 18.12 (CH2), 20.4 (CH 3), 21:31 (CH 3), 25.93 (CH2), 27.30 (CH), 27.80 (CH3), 35.90 (CH2), 47.31 (CH), 68.35 (CH), 72.89 (C) ppm.
MS: m / z (%) = 185 (1) [MH + ], 169 (1), 155 (79), 137 (100), 111 (6), 97 (43), 81 (24), 70 ( 72), 55 (59).
1H-NMR (Mischung der Isomeren, 400 MHz, CDCl3): δ = 1.08 (d, J = 6.2 Hz, 3 H), 1.10 (d, J = 6.1 Hz, 3 H), 1.23 (s, 3 H), 1.32 (s, 3 H), 1.50-1.92 (m, 12 H), 1.63 (dd, J = 1.0 Hz, J=1.4Hz, 3H), 1.70 (dd, J = 0.9 Hz, J = 1.4 Hz, 3 H), 3.62 (dq, J = 6.1 Hz, J = 9.9 Hz, 1 H), 3.72 (dq, J = 6.1 Hz, J = 9.7 Hz, 1 H), 4.70-4.77 (m, 2 H), 4.85-5.23 (m, 2 H), 5.80 (ddd, J = 1.1 Hz, J = 11.0 Hz, J = 5.8 Hz, 2 H), 5.94 (dd, J = 10.8 Hz, J = 17.4 Hz, 2 H) ppm.
13C-NMR (Mischung der Isomeren, 100 MHz, CDCl3): δ = 20.03 (CH3), 20.18 (CH3), 20.28 (CH3), 20.34 (CH3), 25.96 (CH2), 26.54 (CH2), 31.18 (CH3), 34.29 (CH2), 34.74 (CH2), 51.47 (CH), 51.56 (CH), 68.77 (CH), 70.09 (CH), 73.37 (C), 74.92 (C), 111.16 (CH2), 111.47 (CH2), 111.57 (CH2), 114.61 (CH2), 143.17 (CH), 146.36 (CH), 147.30 (C), 147.40 (C) ppm.
MS: m/z (%) = 180 (1) [M+], 165 (1), 136 (8), 121 (18), 107 (16), 93 (35), 79 (11), 68 (100), 53 (16). 1 H-NMR (mixture of isomers, 400 MHz, CDCl 3 ): δ = 1.08 (d, J = 6.2 Hz, 3 H), 1.10 (d, J = 6.1 Hz, 3 H), 1.23 (s, 3 H ), 1.32 (s, 3H), 1.50-1.92 (m, 12H), 1.63 (dd, J = 1.0 Hz, J = 1.4Hz, 3H), 1.70 (dd, J = 0.9Hz, J = 1.4Hz , 3 H), 3.62 (dq, J = 6.1 Hz, J = 9.9 Hz, 1 H), 3.72 (dq, J = 6.1 Hz, J = 9.7 Hz, 1 H), 4.70-4.77 (m, 2 H) , 4.85-5.23 (m, 2H), 5.80 (ddd, J = 1.1 Hz, J = 11.0 Hz, J = 5.8 Hz, 2H), 5.94 (dd, J = 10.8 Hz, J = 17.4 Hz, 2 H ) ppm.
13 C-NMR (mixture of isomers, 100 MHz, CDCl 3 ): δ = 20.03 (CH 3 ), 20.18 (CH 3 ), 20.28 (CH 3 ), 20.34 (CH 3 ), 25.96 (CH 2 ), 26.54 ( CH 2 ), 31.18 (CH 3 ), 34.29 (CH 2 ), 34.74 (CH 2 ), 51.47 (CH), 51.56 (CH), 68.77 (CH), 70.09 (CH), 73.37 (C), 74.92 (C), 111.16 (CH2), 111.47 (CH2), 111.57 (CH2), 114.61 ( CH 2 ), 143.17 (CH), 146.36 (CH), 147.30 (C), 147.40 (C) ppm.
MS: m / z (%) = 180 (1) [M + ], 165 (1), 136 (8), 121 (18), 107 (16), 93 (35), 79 (11), 68 ( 100), 53 (16).
1H-NMR (400 MHz, CDCl3): δ = 0.83 (d, J = 6.6 Hz, 3 H), 0.87 (d, J = 6.8 Hz, 3 H), 1.11-1.29 (m, 2 H), 1.20 (s, 3 H), 1.21 (s, 3 H), 1.42-1.58 (m, 2 H), 1.67 (dd, J = 0.9 Hz, J = 1.4 Hz, 3 H), 1.68-1.88 (m, 4 H), 3.54 (dt, J = 2.5 Hz, J = 9.9 Hz, 1 H), 4.72 (s, br., 2 H) ppm. 13C-NMR (100 MHz, CDCl3): δ = 20.10 (CH3), 21.14 (CH3), 21.89 (CH3), 23.81 (CH), 23.92 (CH3), 26.69 (CH2), 31.75 (CH3), 36.38 (CH2), 42.76 (CH2), 50.50 (CH), 69.95 (CH), 71.08 (C), 111.51 (CH2), 147.55 (C) ppm.
MS: m/z (%) = 210 (1) [M+], 153 (1), 124 (22), 109 (32),95 (6), 81 (10), 68 (100), 57 (8), 41 (21). 1 H-NMR (400 MHz, CDCl 3 ): δ = 0.83 (d, J = 6.6 Hz, 3 H), 0.87 (d, J = 6.8 Hz, 3 H), 1.11-1.29 (m, 2 H), 1.20 (s, 3H), 1.21 (s, 3H), 1.42-1.58 (m, 2H), 1.67 (dd, J = 0.9Hz, J = 1.4Hz, 3H), 1.68-1.88 (m, 4 H), 3.54 (dt, J = 2.5 Hz, J = 9.9 Hz, 1 H), 4.72 (s, br., 2 H) ppm. 13 C-NMR (100 MHz, CDCl 3): δ = 10.20 (CH 3), 21:14 (CH 3), 21.89 (CH3), 23.81 (CH), 23.92 (CH3), 26.69 (CH2), 31.75 (CH 3 ), 36.38 (CH 2 ), 42.76 (CH 2 ), 50.50 (CH), 69.95 (CH), 71.08 (C), 111.51 (CH 2 ), 147.55 (C) ppm.
MS: m / z (%) = 210 (1) [M + ], 153 (1), 124 (22), 109 (32), 95 (6), 81 (10), 68 (100), 57 ( 8), 41 (21).
Bei einer Dosierung von 1% der Aromakomposition im Kaugummi bewirkt das 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran einen deutlichen "Boosteffekt" und vermittelt - im Vergleich zu dem nicht erfindungsgemäßen Aroma - ein verstärktes Frischegefühl, insbesondere in der Anfangsphase des Verzehrs.At a dosage of 1% of the aroma composition in the chewing gum, the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran causes a marked "boost effect" and mediates - In comparison to the flavor not according to the invention - an increased feeling of freshness, especially in the initial phase of consumption.
Bei einer Dosierung von 2% der Aromakomposition im Kaugummi bewirkt das 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran ein verstärktes Frischegefühl und vermittelt - im Vergleich zu dem nicht erfindungsgemäßen Aroma - eine größere Mundfülle, insbesondere beim Kaubeginn.At a dosage of 2% of the flavor composition in the chewing gum, the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran causes an increased feeling of freshness and gives - in comparison to the flavor not according to the invention - a greater mouthfeel, especially at the beginning of chewing.
Bei einer Dosierung von 1% der Aromakomposition in der Zahnpasta bewirkt das 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran bei Bürsten eine Wirkungs-verstärkung des Aromas und vermittelt - im Vergleich zu dem nicht erfindungs-gemäßen Aroma - ein deutliches Frischegefühl, insbesondere beim anfänglichen Bürsten.At a dosage of 1% of the aroma composition in the toothpaste causes the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran in brushes an increase in the effect of the aroma and provides - compared to the non-inventive flavor - a clear feeling of freshness, especially during initial brushing.
Bei einer Dosierung von 1% der Aromakomposition in der Zahnpasta gewinnt die Paste beim Bürsten durch das 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran ein klareres Frischeprofil und vermittelt - im Vergleich zu dem nicht erfindungsgemäßen Aroma - ein eindeutiges retronasales Cooling.At a dosage of 1% of the aroma composition in the toothpaste, the paste gains a clearer freshness profile when brushed by the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran and gives - in comparison to the flavor not according to the invention - a clear retronasal Cooling.
Bei einer Dosierung von 1 % der Aromakomposition in der Zahnpasta gewinnt die Paste beim Bürsten durch das 2,6-Diethyl-5-isopropyl-2-methyl-tetrahydropyran an Mundfülle und erreicht - im Vergleich zu dem nicht erfindungsgemäßen Aroma - ein frischeres Mundgefühl. Zahnpasta III eignet sich insbesondere auch als Zahnpasta für Kinder.At a dosage of 1% of the aroma composition in the toothpaste, the paste gains in brushing by the 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran to mouth fullness and achieved - compared to the non-inventive flavor - a fresher mouthfeel. Toothpaste III is particularly suitable as toothpaste for children.
Bei einer Dosierung von 1% der Aromakomposition in dieser Zahnpasta verbessert sich - im Vergleich zu dem nicht erfindungsgemäßen Aroma - das sensorische Profil deutlich und der Gesamteindruck überzeugt durch vermehrte Frische.At a dosage of 1% of the aroma composition in this toothpaste - compared to the non-inventive aroma - improves the sensory profile significantly and the overall impression convinces by increased freshness.
Bei einer Dosierung von 4% der Aromakomposition in diesem Mundwasser verbessert sich - im Vergleich zu dem nicht erfindungsgemäßen Aroma - der Geschmack überzeugend durch eine stärkere und schnellere Kühlung im Mundraum.At a dosage of 4% of the aroma composition in this mouthwash improved - compared to the non-inventive flavor - the taste convincing by a stronger and faster cooling in the mouth.
45 g dieses Instant-Getränkepulvers wurden in 1000 mL unter Rühren gelöst. Das erhaltene Getränk hatte einen erfrischenden, kühlenden Geschmack von Citrone und Pfefferminze (Variante I) bzw. einen erfrischenden, kühlenden Geschmack von Orange, Zimt und Minze (Variante II).45 g of this instant beverage powder were dissolved in 1000 ml with stirring. The drink obtained had a refreshing, cooling taste of lemon and peppermint (variant I) or a refreshing, cooling taste of orange, cinnamon and mint (variant II).
In Anlehnung an die in
Aroma G hatte dabei folgende Zusammensetzung (Angaben jeweils in Gew.-%): 0, 1 % Neotam Pulver, 29,3% Pfefferminzöl arvensis, Ad 100% Pfefferminz piperita Öl Willamette, 2,27% Sucralose, 0,7% Gewürznelkenöl (clove bud oil), 2,28% Triacetin, 5,4% Diethyltartrat, 12,1% Pfefferminzöl yakima, 0,7% Ethanol, 3,36% 2-Hydroxyethylmenthylcarbonat, 2,6% 2-Hydroxypropylmenthylcarbonat, 5,77% D-Limonen, 5,67% L-Menthylacetat, 0,4% Vitamin E - acetat.Aroma G had the following composition (in each case in wt .-%): 0, 1% neotame powder, 29.3% peppermint oil arvensis, ad 100% peppermint piperita oil Willamette, 2.27% sucralose, 0.7% clove oil ( clove bud oil), 2.28% triacetin, 5.4% diethyl tartrate, 12.1% peppermint oil yakima, 0.7% ethanol, 3.36% 2-hydroxyethylmenthyl carbonate, 2.6% 2-hydroxypropylmenthyl carbonate, 5.77% D-limonene, 5.67% L-menthyl acetate, 0.4% vitamin E acetate.
Die zum Direktverzehr geeigneten Gelatinekapseln I, II, III wurden gemäß
0,05% Isobutyraldehyd, 0,05% 3-Octanol, 0,05% Dimethylsulfid, 0,1% trans-2-Hexenal, 0,1% cis-3-Hexenol, 0, 1 % natürliches 4-Terpineol, 0, 1 % Isopulegol, 0,2% natürliches Piperiton, 0,3% Linalool, 1,0% Isoamylalkohol, 1,0% Isovaleraldehyd, 2,5% natürliches alpha-Pinen, 2,5% natürliches beta-Pinen, 8,0% Eucalyptol, 7,0% I-Menthylacetat, 12,0% I-Menthon, 5,0% Isomenthon, 20,5% I-Carvon, 39,45% I-Menthol.0.05% isobutyraldehyde, 0.05% 3-octanol, 0.05% dimethyl sulfide, 0.1% trans-2-hexenal, 0.1% cis-3-hexenol, 0.1% natural 4-terpineol, 0 , 1% isopulegol, 0.2% natural piperitone, 0.3% linalool, 1.0% isoamyl alcohol, 1.0% isovaleraldehyde, 2.5% natural alpha-pinene, 2.5% natural beta-pinene, 8, 0% Eucalyptol, 7.0% I-menthyl acetate, 12.0% I-menthone, 5.0% isomenthone, 20.5% I-carvone, 39.45% I-menthol.
Die Kaugummibase K1 bestand aus 2,0% Butyl Rubber (Isobuten-Isopren-Copolymer, MW 400,00),400000), 6,0% Polyisobuten (MW = 43,800), 43,5% Polyvinylacetat (MW = 12,000), 31,5% Polyvinylacetat (MW = 47,000), 6,75% Triacetin und 10,25% Calciumcarbonat. Die Herstellung der Kaugummibase K1 und der Kaugummis kann analog zu
Die Kaugummibase K2 bestand aus 28,5% Terpenharz, 33,9% Polyvinylacetat (MW = 14,000), 16,25% hydriertes Pflanzenöl, 5,5% Mono- und Diglyceride, 0,5% Polyisobuten (MW 75,000), 2,0% Butyl Rubber (Isobuten-Isopren-Copolymer), 4,6% amorphes Siliciumdioxid (Wassergehalt ca. 2,5%), 0,05% Antioxidans tert.-Butylhydroxytoluol (BHT), 0,2% Lecitihin, und 8,5% Calciumcarbonat. Die Herstellung der Kaugummibase K2 und der Kaugummis kann analog zu
Die Kaugummis der Rezeptur (I) und (II) wurden als Streifen, die der Rezeptur (III) als Kompaktate in Kissenform hergestellt und anschließend mit Xylit dragiert.The chewing gums of the formulas (I) and (II) were made as strips, the recipe (III) as Kompaktate in pillow form and then coated with xylitol.
Claims (14)
- Alkylated tetrahydropyran of the formula (I):
R2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms, and
R3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
excluding 2,6-dimethyl-3-(1-methylethenyl)-tetrahydropyran, 6-methyl-3-(1-methylethenyl)-2-(2-methylpropyl)-tetrahydropyran, 2-methyl-3-n-propyl-tetrahydropyran and 2-methyl-3-n-butyl-tetrahydropyran. - Alkylated tetrahydropyran according to claim 1, wherein
each R1 independently of each other is a methyl, ethyl or vinyl radical,
R2 is an isopropyl, isopropenyl, sec-butyl or sec-butenyl radical, and
R3 is an unbranched alkyl radical having 1 to 3 C atoms. - Alkylated tetrahydropyran according to one of the preceding claims, wherein
each R1 independently of each other is a methyl or ethyl radical,
R2 is an isopropyl or sec-butyl radical, and
R3 is a methyl or ethyl radical. - Alkylated tetrahydropyran according to one of the preceding claims, chosen from the group consisting of 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran, 2,6-dimethyl-5-isopropyl-2-ethyltetrahydropyran, 2,6-dimethyl-5-isopropenyl-2-vinyltetrahydropyran, 2,6-diethyl-5-sec-butyl-2-methyltetrahydropyran and 2,6-dimethyl-5-sec-butyl-2-ethyltetrahydropyran.
- Mixture comprising or consisting ofa) one, two, three, four or more alkylated tetrahydropyrans according to one of claims 1 to 4,b) one or more (volatile) aroma and/or flavour substances, in particular one or more substance(s) chosen from the group consisting of substances with a physiological cooling action, aroma substances without a physiological cooling action, substances without a physiological cooling action which have a trigeminal or mouth-watering action, and flavour-modulating substances,c) and optionally a cosmetically or pharmaceutically acceptable carrier.
- Mixture according to claim 5, wherein- one or more of the substances with a physiological cooling action are chosen from the group consisting of 1-menthol, isopulegol, menthone glycerol acetal, menthyl lactate, substituted menthane-3-carboxylic acid amides, substituted N-aryl-menthane-3-carboxylic acid amides, substituted N-alkyl-menthane-3-carboxylic acid amides, 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxy-1,2-propanediol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, N-acetylglycine menthyl ester, menthyl hydroxycarboxylic acid esters, menthyl monosuccinate, menthyl monoglutarate, 2-mercaptocyclodecanone, menthyl 2-pyrrolidin-5-onecarboxylate, [N-(4-cyanomethylphenyl)-p-menthanecarboxamide], (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl)cyclohexanecarboxamide, WS-3, WS-23, WS-5, WS-12, WS-14, TPG1™, frescomenthe, p-menthane-3,8-diol, N,N-dimethylmenthylsuccinamide, 6-isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, icilin and icilin derivatives, cubebol, menthyl oxamate, menthyl N-methyloxamate, menthyl N,N-dimethyloxamate, menthyl N-ethyloxamate, menthyl N,N-diethyloxamate, menthyl N-propyloxamate, menthyl N,N-dipropyloxamate, menthyl N-isopropyloxamate, menthyl N,N-diisopropyloxamate, menthyl N-cyclopropyloxamate, menthyl N-butyloxamate, morpholin-4-yl-oxo-acetic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester, menthyl N-(2-methoxyethyl)-oxamate, menthyl N-(3-methoxypropyl)-oxamate, menthyl N-(2-hydroxyethyl)-oxamate, menthyl N-(3-hydroxypropyl)-oxamate,- one or more of the aroma substances without a physiological cooling action are chosen from the group consisting of substances which cause a sharp flavour or a sensation of warmth or heat on skin and mucous membranes or a prickling or tingling feeling in the oral and pharyngeal cavity.
- Mixture according to one of claims 5 or 6, wherein one or more of the substances in constituent b) (i) cause a flavour effect or (ii) cause no flavour effect.
- Formulation for nutrition, oral hygiene or consumption for pleasure or pharmaceutical or cosmetic formulation, comprising (i) one or more alkylated tetrahydropyrans according to one of claims 1 to 4 or (ii) a mixture according to one of claims 5 to 7, wherein constituent (i) or, if present, (ii) is present in a sufficient concentration- to achieve a physiological cooling action on the skin and/or a mucous membrane and/or- to impart, modify or intensify a feeling of freshness in the mouth, pharynx and/or the respiratory tract.
- Formulation according to claim 8, wherein the formulation(i) is a formulation for nutrition or consumption for pleasure chosen from baked goods, confectionery, alcoholic or non-alcoholic drinks, instant drinks, meat products, eggs or egg products, cereal products, dairy products, fruit formulations, vegetable formulations, nibbles, fat- and oil-based products or emulsions thereof, other ready-made dishes and soups, spices, spice mixtures, sprinkling spices, semi-finished goods, food supplements; or(ii) is a formulation for oral hygiene, preferably based on a dental care composition, and is chosen from the group consisting of: toothpaste, dental cream, dental gel, dental powder, tooth-cleaning liquid, tooth-cleaning foam, mouthwash, dental cream and mouthwash as a 2-in-1 product, bonbon for sucking, oral spray, dental floss and dental care chewing gum; or(iii) is a pharmaceutical formulation, the formulation being a preferably oral or nasal pharmaceutical formulation, preferably in the form of capsules, tablets, coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, emulsions, powders, solutions, pastes or another formulation which can be swallowed or chewed; or(iv) is a cosmetic formulation chosen from the group consisting of: soap, syndet, liquid washing, showering or bathing preparation, emulsion, ointment, paste, gel, oil, toner, balsam, serum, powder, eau de toilette, toilette, eau de Cologne, perfume, wax, stick, roll-on, (pump) spray, aerosol (foaming, non-foaming or after-foaming), foot care composition, beard cleaning or care composition, insect-repellent composition, sunscreen composition, after-sun preparation, shaving composition, after-shave, depilatory composition, hair care composition, conditioner, hair tonic, hair lotion, hair rinse, styling cream, pomade, permanent wave and setting composition, hair smoothing composition, hair setting agent, styling aid, blonding composition, hair lightener, hair conditioner, hair mousse, hair tint, nail care composition, deodorant, antiperspirant, mouthwash, mouth spray, make-up, make-up remover, eye care, lip cosmetics, lip care composition, decorative cosmetics, bathing article and mask.
- Use (i) of an alkylated tetrahydropyran of the formula (I) :
and R2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms
and R3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
or (ii) of a mixture according to one of claims 5 to 7- for generating a cooling action on the skin and/or a mucous membrane for other than therapeutic purposes and/or- for imparting, modifying or intensifying a feeling of freshness in the mouth, pharynx and/or the respiratory tract for other than therapeutic purposes. - Use (i) of an alkylated tetrahydropyran of the formula (I) :
and R2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms
and R3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
or (ii) of a mixture according to one of claims 5 to 7
for the preparation of a medicament. - Use according to claim 11 for the preparation of a medicament, wherein the medicament to be prepared is for combating or alleviating cough, cold, inflammation, sore throat or hoarseness symptoms.
- Non-therapeutic method (a) for generating a cooling action on the skin and/or a mucous membrane and/or (b) for imparting, modifying or intensifying a feeling of freshness in the mouth, pharynx and/or the respiratory tract, with the following step:application of an amount sufficient to achieve the action (a) and/or (b) (i) of an alkylated tetrahydropyran of the formula (I):
and R2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms
and R3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
or (ii) of a mixture according to one of claims 5 to 7, to the skin and/or a mucous membrane. - Process for the preparation of an alkylated tetrahydropyran of the formula (I):
and R2 is a branched or unbranched alkyl or alkenyl radical having 3 to 4 C atoms
and R3 is a branched or unbranched alkyl radical having 1 to 5 C atoms,
comprising the steps:- reaction of the aldehyde (B) with the alcohol component (A) to give the corresponding cyclized tetrahydropyran compound (C),- optionally reduction of the tetrahydropyran compound (C) to give the tetrahydropyran compound (D)
R1 and R3 in each case have the abovementioned (optionally preferred) meaning, and
Ra, Rb and Rc independently of each other can represent methyl or ethyl, with the proviso that Ra, Rb and Rc contain 1 or 2 C atoms in total.
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US15816209P | 2009-03-06 | 2009-03-06 |
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EP2168957A2 EP2168957A2 (en) | 2010-03-31 |
EP2168957A3 EP2168957A3 (en) | 2010-07-28 |
EP2168957B1 true EP2168957B1 (en) | 2012-02-15 |
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EP09176696A Active EP2168957B1 (en) | 2009-03-06 | 2009-11-20 | Alkyl-substituted tetrahydropyranes as aromatic materials |
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US (1) | US8242289B2 (en) |
EP (1) | EP2168957B1 (en) |
AT (1) | ATE545639T1 (en) |
ES (1) | ES2379751T3 (en) |
Cited By (1)
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RU2724996C2 (en) * | 2015-06-30 | 2020-06-29 | Вм. Ригли Джр. Компани | Cooling compositions of long action |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7810507B2 (en) * | 2006-02-10 | 2010-10-12 | R. J. Reynolds Tobacco Company | Smokeless tobacco composition |
GB201103103D0 (en) * | 2011-02-23 | 2011-04-06 | Givaudan Sa | Organic compounds |
EP2497458A1 (en) * | 2011-03-08 | 2012-09-12 | B.R.A.I.N. Biotechnology Research And Information Network AG | Small molecule modulators of the cold and menthol receptor TRPM8 |
BR112014017791B1 (en) * | 2012-01-18 | 2019-06-25 | International Flavors & Fragrances Inc | Octahydro-benzofurans and their uses in perfume compositions |
EP3219303B1 (en) * | 2012-01-30 | 2019-11-06 | Symrise AG | Compositions |
CN104394718A (en) * | 2012-07-02 | 2015-03-04 | 西姆莱斯股份公司 | A method of flavouring a smoking product |
US9581255B2 (en) | 2012-07-23 | 2017-02-28 | Henning, Inc. | Multiple proportion delivery systems and methods |
JP6185523B2 (en) * | 2015-09-03 | 2017-08-23 | 三栄源エフ・エフ・アイ株式会社 | Bitter taste masking method for perfume solvent |
CN106262580A (en) * | 2016-08-08 | 2017-01-04 | 安徽丰乐香料有限责任公司 | A kind of coolant agent N (4 methoxyphenyl) using method to menthyl 3 carboxylic acid amides |
FR3060346B1 (en) * | 2016-12-20 | 2020-01-03 | L'oreal | HAIR LIGHTENING COMPOSITION COMPRISING AN OXIDIZING AGENT, BICARBONATE, AND AT LEAST 0.5% BY WEIGHT OF POLYPHOSPHORUS DERIVATIVE |
JP2018203645A (en) * | 2017-05-31 | 2018-12-27 | ライオン株式会社 | Composition for oral cavity |
EP3466938A1 (en) | 2017-10-05 | 2019-04-10 | Basf Se | 3,5-diethyl-2-propyl-tetrahydropyran and stereoisomers thereof for use as aroma chemicals |
CN113181770B (en) * | 2021-04-27 | 2022-08-19 | 晨光生物科技集团股份有限公司 | Application of organic solvent-resistant nanofiltration membrane in capsorubin peppery removal |
CN115872881A (en) * | 2022-11-14 | 2023-03-31 | 云南中烟工业有限责任公司 | Synthesis method of menthol amine compound and application of menthol amine compound in cigarettes |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4518615A (en) | 1983-08-23 | 1985-05-21 | Warner-Lambert Company | Non-adhesive chewing gum base composition |
US4721620A (en) | 1986-04-01 | 1988-01-26 | Warner-Lambert Company | Polyvinylacetate bubble gum base composition |
US5002791A (en) | 1988-10-28 | 1991-03-26 | Warner-Lambert Company | Process for forming a confectionary rope having a viscous center |
US5093136A (en) | 1991-05-08 | 1992-03-03 | Nabisco Brands, Inc. | Dual gum base bubble gum |
US5266336A (en) | 1991-11-12 | 1993-11-30 | Wm. Wrigley Jr. Company | High flavor impact non-tack chewing gum with reduced plasticization |
US5137741A (en) | 1991-12-19 | 1992-08-11 | International Flavors & Fragrances Inc. | Flavoring with reaction product of linalool with citric acid |
US5458894A (en) | 1994-01-14 | 1995-10-17 | Warner-Lambert Company | Apparatus and method for automatically controlling the speed of a candy forming machine |
US5589158A (en) | 1994-11-17 | 1996-12-31 | Bush Boake Allen Inc. | Flavor enhancer |
US5601858A (en) | 1994-12-29 | 1997-02-11 | Warner-Lambert Company | Non-stick chewing gum |
GB9707978D0 (en) | 1997-04-21 | 1997-06-11 | Procter & Gamble | Throat soothing compositions |
EP1025200B1 (en) | 1997-10-23 | 2004-05-26 | Quest International B.V. | Improving the flavour of fermented beverages |
DE10058459A1 (en) | 2000-11-24 | 2002-06-06 | Haarmann & Reimer Gmbh | rhinologically |
US6986709B2 (en) | 2001-09-21 | 2006-01-17 | Igt | Gaming device having games with variable game functions |
DE10225350A1 (en) | 2002-06-07 | 2003-12-18 | Symrise Gmbh & Co Kg | Use of 1,3-dioxanes as flavors, especially for flavoring foods, consumables, body care products or pharmaceutical preparations |
DE10227462A1 (en) | 2002-06-20 | 2004-01-08 | Symrise Gmbh & Co. Kg | Production of cis-pellitor and use as a flavoring |
DE10253331A1 (en) | 2002-11-14 | 2004-06-03 | Symrise Gmbh & Co. Kg | Use of trans-pellitori as a flavoring |
ES2272632T3 (en) | 2002-12-05 | 2007-05-01 | SYMRISE GMBH & CO. KG | SEEDING CAPSULES WITH SEWING CIN. |
US6986907B2 (en) | 2003-07-28 | 2006-01-17 | Wm. Wrigley Jr. Company | Chewing gum base and chewing gum compositions |
DE10351422A1 (en) | 2003-11-04 | 2005-06-16 | Symrise Gmbh & Co. Kg | Use of alkenecarboxylic acid N-alkylamides as flavoring agents |
DE502007000290D1 (en) * | 2006-04-19 | 2009-01-29 | Symrise Gmbh & Co Kg | New Uses of Nonenolide |
WO2008138162A1 (en) | 2007-05-16 | 2008-11-20 | Givaudan Sa | Compositions and their use |
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RU2724996C2 (en) * | 2015-06-30 | 2020-06-29 | Вм. Ригли Джр. Компани | Cooling compositions of long action |
Also Published As
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US20100226864A1 (en) | 2010-09-09 |
EP2168957A3 (en) | 2010-07-28 |
ES2379751T3 (en) | 2012-05-03 |
ATE545639T1 (en) | 2012-03-15 |
EP2168957A2 (en) | 2010-03-31 |
US8242289B2 (en) | 2012-08-14 |
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